* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃;
Methyl E-3-(3’-Adamantan-1-yl-4’-hydroxybiphenyl-4-yl)acrylate. (3.28 g, 8.45 mmol) was added to asolution of LiOH.H2O (1.77 g, 42.25 mmol) in 340 mL of THF/H2O, 1:1, and the mixture was kept under stirring at room temperature overnight. The THF was evaporated and the mixture was extracted with hexane, acidified with 2 N HCl, and filtered to give 2.82 g (94percent) of the title compound, mp >240 °C. 1H NMR (DMSO-d6) : 1.74 (6H, s, 6Ad), 2.04 (3H, s, 3Ad), 2.12 (6H, s, 6Ad.), 6.51 (1H, d, -CH, J = 16.1 Hz), 6.85 (1H, d, 1Ar, J = 8.8 Hz), 7.30-7.40 (2H, m, 2Ar), 7.55-7.63 (3H, m, 2Ar + CH), 7.70 (2H, d, 2Ar, J = 8.0 Hz), 9.54 (1H, s, -OH), 12.34 (1H, brs, -COOH). MS (m/z): 374 (M+, 100).
Reference：
[1] Journal of Medicinal Chemistry, 2003, vol. 46, # 6, p. 909 - 912
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 15, p. 4931 - 4946
[3] European Journal of Medicinal Chemistry, 2014, vol. 79, p. 251 - 259
2
[ 1232885-04-9 ]
[ 496868-77-0 ]
Yield
Reaction Conditions
Operation in experiment
12 %Chromat.
With water In dimethyl sulfoxide at 37℃; for 24 h; aq. buffer
General procedure: Chemical stability of Adarotene derivatives was ascertained at 37 °C at the stomach pH (1.2), intestine pH (6.8) and blood pH (7.4). Due to the low water solubility of the compounds, stability experiments were performed in aqueous buffer containing 5percent DMSO and 5percent Tween 80. The stability results are reported (Table 1a, S.I.) as percentage of recovery, as determined by HPLC and UPLC measurements (see Section 5). All compounds appeared unchanged after 12 h at pH 1.2. Compounds 6b-d, 6h and 7b were partially hydrolysed at pH 6.8 and 7.4, with the lowest percentage of recovery for 6d and 7b (12percent and 36percent resp.) at pH 7.4. All the partially hydrolysed compounds contain a basic nitrogen in the side chain.
Reference：
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
3
[ 1232886-41-7 ]
[ 496868-77-0 ]
Yield
Reaction Conditions
Operation in experiment
38 %Chromat.
With water In dimethyl sulfoxide at 37℃; for 24 h; aq. buffer
General procedure: Chemical stability of Adarotene derivatives was ascertained at 37 °C at the stomach pH (1.2), intestine pH (6.8) and blood pH (7.4). Due to the low water solubility of the compounds, stability experiments were performed in aqueous buffer containing 5percent DMSO and 5percent Tween 80. The stability results are reported (Table 1a, S.I.) as percentage of recovery, as determined by HPLC and UPLC measurements (see Section 5). All compounds appeared unchanged after 12 h at pH 1.2. Compounds 6b-d, 6h and 7b were partially hydrolysed at pH 6.8 and 7.4, with the lowest percentage of recovery for 6d and 7b (12percent and 36percent resp.) at pH 7.4. All the partially hydrolysed compounds contain a basic nitrogen in the side chain.
Reference：
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
4
[ 1370009-35-0 ]
[ 496868-77-0 ]
Yield
Reaction Conditions
Operation in experiment
64 %Chromat.
With water In dimethyl sulfoxide at 37℃; for 24 h; aq. buffer
General procedure: Chemical stability of Adarotene derivatives was ascertained at 37 °C at the stomach pH (1.2), intestine pH (6.8) and blood pH (7.4). Due to the low water solubility of the compounds, stability experiments were performed in aqueous buffer containing 5percent DMSO and 5percent Tween 80. The stability results are reported (Table 1a, S.I.) as percentage of recovery, as determined by HPLC and UPLC measurements (see Section 5). All compounds appeared unchanged after 12 h at pH 1.2. Compounds 6b-d, 6h and 7b were partially hydrolysed at pH 6.8 and 7.4, with the lowest percentage of recovery for 6d and 7b (12percent and 36percent resp.) at pH 7.4. All the partially hydrolysed compounds contain a basic nitrogen in the side chain.
Reference：
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
5
[ 1232885-35-6 ]
[ 496868-77-0 ]
Yield
Reaction Conditions
Operation in experiment
15 %Chromat.
With water In dimethyl sulfoxide at 37℃; for 24 h; aq. buffer
General procedure: Chemical stability of Adarotene derivatives was ascertained at 37 °C at the stomach pH (1.2), intestine pH (6.8) and blood pH (7.4). Due to the low water solubility of the compounds, stability experiments were performed in aqueous buffer containing 5percent DMSO and 5percent Tween 80. The stability results are reported (Table 1a, S.I.) as percentage of recovery, as determined by HPLC and UPLC measurements (see Section 5). All compounds appeared unchanged after 12 h at pH 1.2. Compounds 6b-d, 6h and 7b were partially hydrolysed at pH 6.8 and 7.4, with the lowest percentage of recovery for 6d and 7b (12percent and 36percent resp.) at pH 7.4. All the partially hydrolysed compounds contain a basic nitrogen in the side chain.
Reference：
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
6
[ 496868-80-5 ]
[ 496868-77-0 ]
Reference：
[1] Journal of Medicinal Chemistry, 2005, vol. 48, # 15, p. 4931 - 4946
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 6, p. 909 - 912
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
[5] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
[6] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
[7] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
[8] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
[9] European Journal of Medicinal Chemistry, 2014, vol. 79, p. 251 - 259
7
[ 768-95-6 ]
[ 496868-77-0 ]
Reference：
[1] Journal of Medicinal Chemistry, 2005, vol. 48, # 15, p. 4931 - 4946
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 6, p. 909 - 912
[3] European Journal of Medicinal Chemistry, 2014, vol. 79, p. 251 - 259
8
[ 29558-77-8 ]
[ 496868-77-0 ]
Reference：
[1] Journal of Medicinal Chemistry, 2005, vol. 48, # 15, p. 4931 - 4946
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 6, p. 909 - 912
[3] European Journal of Medicinal Chemistry, 2014, vol. 79, p. 251 - 259
9
[ 1232884-73-9 ]
[ 496868-77-0 ]
Reference：
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
[5] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
[6] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
10
[ 1232886-30-4 ]
[ 496868-77-0 ]
Reference：
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
11
[ 1232885-10-7 ]
[ 496868-77-0 ]
Reference：
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
12
[ 1232886-46-2 ]
[ 496868-77-0 ]
Reference：
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
13
[ 1370009-41-8 ]
[ 496868-77-0 ]
Reference：
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2405 - 2415
With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20℃;
Methyl E-3-(3?-Adamantan-1-yl-4?-hydroxybiphenyl-4-yl)acrylate. (3.28 g, 8.45 mmol) was added to asolution of LiOH.H2O (1.77 g, 42.25 mmol) in 340 mL of THF/H2O, 1:1, and the mixture was kept under stirring at room temperature overnight. The THF was evaporated and the mixture was extracted with hexane, acidified with 2 N HCl, and filtered to give 2.82 g (94%) of the title compound, mp >240 C. 1H NMR (DMSO-d6) : 1.74 (6H, s, 6Ad), 2.04 (3H, s, 3Ad), 2.12 (6H, s, 6Ad.), 6.51 (1H, d, -CH, J = 16.1 Hz), 6.85 (1H, d, 1Ar, J = 8.8 Hz), 7.30-7.40 (2H, m, 2Ar), 7.55-7.63 (3H, m, 2Ar + CH), 7.70 (2H, d, 2Ar, J = 8.0 Hz), 9.54 (1H, s, -OH), 12.34 (1H, brs, -COOH). MS (m/z): 374 (M+, 100).
3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)-N-hydroxyacrylamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
54%
General procedure: To a suspension of the appropriate acid (0.53mmol) in dry DMF (8.3mL) HOBt (86mg, 0.64mmol) and WSC (132mg, 0.69mmol) were added. The mixture was stirred at room temperature under nitrogen for 1.5-24h, then NH2OH·HCl (185mg, 2.66mmol) and TEA (368muL, 2.66mmol) were added. The reaction was stirred at room temperature for 1-4h. After addition of water, a precipitate formed, which was filtered and dried to obtain the desired hydroxamic acid.
To a solution of £-4-(3-(1-adamantyl)-4-hydroxyphenyl)cinnamic acid (2 g, 5.34 mmol) in 80 ml of DMF were added hydroxybenzotriazole hydrate (866 mg, 5.34 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (1130 mg, 6.94 mmol). The mixture was stirred at room temperature for 4h. After addition of hydroxylamine hydrochloride (1856 mg , 26.7 mmol), followed by 3.7 ml (26.7 mmol) of TEA, the mixture was stirred at room temperature overnight. DMF was removed under reduced pressure and the residue was washed with water to obtain 5g of a crude product. Purification by flash chromatography on silica gel (phosphate buffered) using as eluent dichloromethane/methanol 95:5 afforded 950 mg of the title compound as a white solid. M. p. 210-2120C dec. Rf = 0.19 (Merck silica gel 60F254, Hexane/ EtOAc 4:6) 1HNMR (DMSO-de) delta: 1.73 (6H, s, 6Ad.); 2.04 (3H, s, 3Ad.); 2.13 (6H, s, 6Ad.); 6.46 (1 H, d, -CH=, J = 16.00 Hz); 6.86 (1 H, d, 1Ar, J = 8.19 Hz); 7.29-7.40 (2H, m, 2Ar); 7.47 (1 H, d, EPO <DP n="13"/>-CH=, J = 16.00 Hz); 7.52-7.65 (4H, m, 4Ar); 9.03 (1 H, brs, -CONHOH); 9.54 (1 H, s, -OH);10.75 (1 H, brs, -CONHOH).
Example 24: (E)-Methanesulfonic acid 3-adamantan-l-yl-4'-(2-carboxyvinyl)- biphenyl-4-yl ester ST7259AA1; Methanesulfonyl chloride (91.8 mg, 0.802 mmol) and triethylamine (162 mg,1.60 mmol) were added to a solution of (E)-3-(3'-adamantan-l-yl-4'-hydroxy- biphenyl-4-yl)-acrylic acid (150 mg, 0.401 mmol) in THF (1.60 ml) at 0C and the resulting mixture was stirred for Ih. The latter was diluted with EtOAc, washed with IN HCl and dried over Na2SO4 and concentrated in vacuo. The residue was purified by crystallization from EtOAc/isopropyl ether 1:1 to afford 20 mg (11%) of product as a white powder.1H NMR (DMSO-ds) delta: 7.83-7.69 (m, 4H), 7.65(dd, J= 7.96 Hz, J= 2.32 Hz, IH),7.61 (IH, s), 7.58 (d, J= 16.03 Hz, IH), 7.54 (d, J= 7.96 Hz, IH), 6.58 (d, J= 16.03 Hz, IH), 3.61 (s, 3H), 2.09 (s, 9H), 1.75 (s, 6H).
With morpholine; In N,N-dimethyl-formamide; at 20℃; for 0.333333h;
Example 16: (E)-cyclopropanecarboxylic acid 3-adamantan-l-yl-4'-(2- carboxyvinyl)-biphenyl-4-yl ester ST5610AA1; STEP 1: To a suspension of 3-(3'-adamantan-l-yl-4'-hydroxy-biphenyl-4-yl)- acrylic acid (200 mg, 0.534 mmol) in DMF (3 ml), morpholine (60 mg, 0.694 mmol) and TBDPSiCl (166 mg, 0.587 mmol) were added. The resulting mixture was stirred at RT for 20 min and then diluted with DCM. The organic solution was washed several times with water, dried over Na2SO4, filtered and concentrated in vacuo. The resulting product was purified on silica gel (ethyl acetate: hexane 15:85) to obtain (E)-3-(3'-adamantan-l-yl-4'-hydroxybiphenyl- 4-yl)acrylic acid £er£-butyldiphenylsilyl ester (237 mg, 72%).1H NMR (DMSO-ds) delta: 9.6 (s, IH); 7.60-7.85 (m, 10H); 7.35-7.55 (m, 8H); 6.89 (d, J = 8.6 Hz, IH); 6.78 (d, J = 16 Hz, IH); 2.13 (s, 6H); 2.04 (s, 3H); 1.75 (s, 6H); 1.1 (s, 9H).
72%
With morpholine; In N,N-dimethyl-formamide; at 20℃; for 0.333333h;Inert atmosphere;
Morpholine (1.3 equiv) was added to a suspension of (E)-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl) acrylic acid (200 mg, 0.534 mmol) in DMF (3 mL). TBDPSCl (1.1 equiv) was added via siringe upon rigorous stirring. The reaction mixture was allowed to stir for 20 min under nitrogen, at room temperature, then diluted with CH2Cl2 and washed several times with water. The organic layer was evaporated and the crude was purified by flash chromatography (hexane/ethyl acetate 85:15) to give 237 mg of (E)-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl) acrylic acid tert-butyldiphenylsilyl ester as a yellow solid. Yield 72%. 1H NMR (300 MHz, DMSO-d6) delta 9.59 (s, 1H), 7.87-7.61 (m, 9H), 7.56-7.36 (m, 8H), 6.88 (d, J = 8.6 Hz, 1H), 6.75 (d, J = 16.0 Hz, 1H), 2.27-2.0 (m, 9H), 1.74 (s, 6H), 1.09 (s, 9H).
Example 12: (E)-3-(3'-adamantan-l-yl-4'-isopropylcarbamoyloxy-biphenyl-4- yl)-acrylic acid ST5536AA1; Isopropyl isocyanate (327 mul, 3.33mmol) was added at RT to a solution of (E)- 3-(3'-adamantan-l-yl-4'-hydroxy-biphenyl-4-yl)-acrylic acid (200 mg, 0.53 mmol),NEt3 (314 mul, 2.44mmol) and the reaction mixture was stirred for 5 days. The reaction mixture was diluted with DCM and washed with H2O. The organic phase was dried over Na2SO4 and the solvent was removed under reduced pressure.The desired compound was obtained without any further purification as a solid in 68% yield.1H-NMR (300 MHz, DMSO-ds) delta: 12.40 (bs, IH); 7.7 (bd, H); 7.74 (d, J=8.2 Hz, 2H); 7.67 (d, J=8.2 Hz, 2H); 7.60 (d, J=15.9 Hz, IH); 7.51 (m, 2H); 7.04 (d,J=8.9 Hz, IH); 6.58 (d, J=15.9 Hz, IH); 3.70 (m,lH); 2.02 (bs, 9H); 1.74 (m, 6H);1.14 (s, 3H); 1.12 (s, 3H).ESI-MS m/z = 458.1 [M-H]-.
68%
With triethylamine; In dichloromethane; at 20℃; for 120h;
Isopropyl isocyanate (327 muL, 3.33 mmol) was added to a solution of (E)-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl) acrylic acid (200 mg, 0.534 mmol) and NEt3 (314 muL, 2.44 mmol) in anhydrous DCM (8 mL). The reaction mixture was stirred for 5 days at room temperature. The reaction mixture was diluted with DCM and washed with H2O. The organic phase was dried over Na2SO4 and the solvent was removed under reduced pressure. The desired compound was obtained without any further purification as a white powder (7a). Yield 68%, 1H NMR (300 MHz, DMSO-d6) 12.40 (br s, 1H); 7.7 (br d, H); 7.74 (d, J = 8.2 Hz, 2H); 7.67 (d, J = 8.2 Hz, 2H); 7.60 (d, J = 15.9 Hz, 1H); 7.51 (m, 2H); 7.04 (d, J = 8.9 Hz, 1H); 6.58 (d, J = 15.9 Hz, 1H); 3.70 (m,1H); 2.02 (br s, 9H); 1.74 (m, 6H); 1.14 (s, 3H); 1.12 (s, 3H). ESI-MS m/z = 458.1 [M-H]-.
With water; In dimethyl sulfoxide; at 37℃; for 24h;pH 7.4;aq. buffer;
General procedure: Chemical stability of Adarotene derivatives was ascertained at 37 C at the stomach pH (1.2), intestine pH (6.8) and blood pH (7.4). Due to the low water solubility of the compounds, stability experiments were performed in aqueous buffer containing 5% DMSO and 5% Tween 80. The stability results are reported (Table 1a, S.I.) as percentage of recovery, as determined by HPLC and UPLC measurements (see Section 5). All compounds appeared unchanged after 12 h at pH 1.2. Compounds 6b-d, 6h and 7b were partially hydrolysed at pH 6.8 and 7.4, with the lowest percentage of recovery for 6d and 7b (12% and 36% resp.) at pH 7.4. All the partially hydrolysed compounds contain a basic nitrogen in the side chain.
With water; In dimethyl sulfoxide; at 37℃; for 24h;pH 7.4;aq. buffer;
General procedure: Chemical stability of Adarotene derivatives was ascertained at 37 C at the stomach pH (1.2), intestine pH (6.8) and blood pH (7.4). Due to the low water solubility of the compounds, stability experiments were performed in aqueous buffer containing 5% DMSO and 5% Tween 80. The stability results are reported (Table 1a, S.I.) as percentage of recovery, as determined by HPLC and UPLC measurements (see Section 5). All compounds appeared unchanged after 12 h at pH 1.2. Compounds 6b-d, 6h and 7b were partially hydrolysed at pH 6.8 and 7.4, with the lowest percentage of recovery for 6d and 7b (12% and 36% resp.) at pH 7.4. All the partially hydrolysed compounds contain a basic nitrogen in the side chain.
(S)-2-amino-3-methyl-butyric acid 3-adamantan-1-yl-4'-((E)-2-carboxyvinyl)biphenyl-4-yl ester trifluoroacetate[ No CAS ]
[ 496868-77-0 ]
Yield
Reaction Conditions
Operation in experiment
88%Chromat.
With water; In dimethyl sulfoxide; at 37℃; for 24h;pH 7.4;aq. buffer;
General procedure: Chemical stability of Adarotene derivatives was ascertained at 37 C at the stomach pH (1.2), intestine pH (6.8) and blood pH (7.4). Due to the low water solubility of the compounds, stability experiments were performed in aqueous buffer containing 5% DMSO and 5% Tween 80. The stability results are reported (Table 1a, S.I.) as percentage of recovery, as determined by HPLC and UPLC measurements (see Section 5). All compounds appeared unchanged after 12 h at pH 1.2. Compounds 6b-d, 6h and 7b were partially hydrolysed at pH 6.8 and 7.4, with the lowest percentage of recovery for 6d and 7b (12% and 36% resp.) at pH 7.4. All the partially hydrolysed compounds contain a basic nitrogen in the side chain.
With water; In dimethyl sulfoxide; at 37℃; for 24h;pH 7.4;aq. buffer;
General procedure: Chemical stability of Adarotene derivatives was ascertained at 37 C at the stomach pH (1.2), intestine pH (6.8) and blood pH (7.4). Due to the low water solubility of the compounds, stability experiments were performed in aqueous buffer containing 5% DMSO and 5% Tween 80. The stability results are reported (Table 1a, S.I.) as percentage of recovery, as determined by HPLC and UPLC measurements (see Section 5). All compounds appeared unchanged after 12 h at pH 1.2. Compounds 6b-d, 6h and 7b were partially hydrolysed at pH 6.8 and 7.4, with the lowest percentage of recovery for 6d and 7b (12% and 36% resp.) at pH 7.4. All the partially hydrolysed compounds contain a basic nitrogen in the side chain.
With water; In dimethyl sulfoxide; at 37℃; for 24h;pH 7.4;aq. buffer;
General procedure: Chemical stability of Adarotene derivatives was ascertained at 37 C at the stomach pH (1.2), intestine pH (6.8) and blood pH (7.4). Due to the low water solubility of the compounds, stability experiments were performed in aqueous buffer containing 5% DMSO and 5% Tween 80. The stability results are reported (Table 1a, S.I.) as percentage of recovery, as determined by HPLC and UPLC measurements (see Section 5). All compounds appeared unchanged after 12 h at pH 1.2. Compounds 6b-d, 6h and 7b were partially hydrolysed at pH 6.8 and 7.4, with the lowest percentage of recovery for 6d and 7b (12% and 36% resp.) at pH 7.4. All the partially hydrolysed compounds contain a basic nitrogen in the side chain.
With water; In dimethyl sulfoxide; at 37℃; for 24h;pH 7.4;aq. buffer;
General procedure: Chemical stability of Adarotene derivatives was ascertained at 37 C at the stomach pH (1.2), intestine pH (6.8) and blood pH (7.4). Due to the low water solubility of the compounds, stability experiments were performed in aqueous buffer containing 5% DMSO and 5% Tween 80. The stability results are reported (Table 1a, S.I.) as percentage of recovery, as determined by HPLC and UPLC measurements (see Section 5). All compounds appeared unchanged after 12 h at pH 1.2. Compounds 6b-d, 6h and 7b were partially hydrolysed at pH 6.8 and 7.4, with the lowest percentage of recovery for 6d and 7b (12% and 36% resp.) at pH 7.4. All the partially hydrolysed compounds contain a basic nitrogen in the side chain.
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 2h;
Acetyl chloride (74 muL, 1.05 mmol) was added to a solution of <strong>[496868-77-0](E)-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid</strong> (156 mg, 0.42 mmol), DIPEA (290 muL, 1.68 mmol) in DCM (5 mL). The reaction mixture was allowed to stir for 2 h at room temperature, then diluted with CH2Cl2 and washed several times with water. The organic phase was concentrated under reduced pressure and the crude product was subsequent hydrolysed in THF/water 1:1. After complete conversion (4 h), DMF and brine were added and the organic phase was separated, dried over Na2SO4, filtered and concentrated. The white solid obtained was washed with Et2O and dried to give 145 mg of the title compound (6a).
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