182570-26-9|6-Methoxychroman-3-carboxylic acid| Ambeed

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Quality Control of [ 182570-26-9 ] Purity: 98% SDS Specification

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Product Details of [ 182570-26-9 ]

CAS No. :	182570-26-9
Formula :	C₁₁H₁₂O₄
M.W :	208.21
SMILES Code :	O=C(C1COC2=C(C=C(OC)C=C2)C1)O
MDL No. :	MFCD04114628
InChI Key :	YFYLMFXPYODSEB-UHFFFAOYSA-N
Pubchem ID :	3163251

Safety of [ 182570-26-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 182570-26-9 ]

* 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.

Downstream synthetic route of [ 182570-26-9 ]

[ 182570-26-9 ] Synthesis Path-Downstream 1~35

1
[ 182570-26-9 ]
[ 942076-84-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6390 - 6393.

2
[ 182570-26-9 ]
[ 38191-34-3 ]
[ 1213262-03-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 3h;	To a solution of the 1-1 and -methoxychroman-S-carboxylic acid in DMF were added HATU (1.1 equiv) and DIEA (3 equiv). The resulting mixture was stirred at room temperature for 3h. The solution was diluted with EtOAc and washed with saturated aqueous sodium bicarbonate solution. The organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give bromide 1-2 (95% yield).

References: [1]Patent: WO2010/24903,2010,A1 .Location in patent: Page/Page column 52-53.
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6390 - 6393.

3
[ 182570-26-9 ]
[ 1575-37-7 ]
C₁₇H₁₇BrN₂O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6390 - 6393.

4
[ 182570-26-9 ]
[ 1072906-05-8 ]
C₂₁H₂₅BrN₂O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6406 - 6409.

5
[ 182570-26-9 ]
[ 19056-40-7 ]
C₁₈H₁₈BrNO₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6406 - 6409.

6
[ 182570-26-9 ]
[ 59557-91-4 ]
[ 1161763-22-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6406 - 6409.

7
[ 182570-26-9 ]
[ 106-40-1 ]
[ 1161762-49-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6406 - 6409.

8
[ 885271-71-6 ]
[ 182570-26-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6406 - 6409.

9
C₁₈H₁₆O₄ [ No CAS ]
[ 182570-26-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6406 - 6409.

10
[ 672-13-9 ]
[ 2495-35-4 ]
[ 182570-26-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1939 - 1943.

11
[ 182570-26-9 ]
C₁₀H₁₆BrN₃O [ No CAS ]
C₂₁H₂₄BrN₃O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1939 - 1943.

12
[ 182570-26-9 ]
C₉H₁₃BrN₂O₂ [ No CAS ]
C₂₀H₂₁BrN₂O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1939 - 1943.

13
[ 182570-26-9 ]
[ 1575-37-7 ]
C₁₇H₁₅BrN₂O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1939 - 1943.

14
[ 182570-26-9 ]
[ 60719-84-8 ]
[ 1213262-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;	To a solution of 6-1 (1 equiv), DIEA (5 equiv), and 6-methoxy-3- carboxylic acid (1.1 equiv) in DMF was added HATU (1.1 equiv). After stirring the solution at room temperature overnight (LC-MS showed complete reaction), the solvents were removed in vacuum. The residue was suspended in ethyl acetate, and washed by brine (2x), saturated sodium bicarbanate (3x), and brine (3x), dried over sodium sulfate, and evaporated in vacuum to give crude amide 6-2. This crude intermediate was used directly in the next step without further purification. Thus, Lawesson's reagent (0.5 equiv) was added to a suspension of crude 6-2 in toluene. The suspension was heated at 95 C overnight. The solvents were removed in vacuum, and the residue was subjected to preparative HPLC to give the final product 6-3 (Example 149).

References: [1]Patent: WO2010/24903,2010,A1 .Location in patent: Page/Page column 95-96.

15
[ 182570-26-9 ]
[ 1227361-53-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1844 - 1848.

16
[ 182570-26-9 ]
[ 1295570-15-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1844 - 1848.

17
[ 182570-26-9 ]
[ 1227361-52-5 ]
C₁₈H₁₅BrN₂O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1844 - 1848.

18
[ 2033-24-1 ]
[ 182570-26-9 ]
[ 1296201-69-8 ]

Yield	Reaction Conditions	Operation in experiment
72%		Oxalyl chloride (1.5 equiv) and dry DMF (4 drops) were added to the mixture of 6- methoxylchroman-3-carboxylic acid (1 equiv) in dry DCM (2 mL). After stirring 4 hours, the solvent was removed under reduced pressure and the remaining residue was resolved in dry DCM (2 mL) and added to the mixture of Meldrum's acid (1 equiv) and pyridine (3 equiv) in DCM (2 mL) at 0 C. After stirring at room temperature for 30 min, the reaction was quenched with water and the organic phase was extract with DCM, dried over anhydrous Na2S04, concentrated under reduced pressure, and purified over silica gel to give 5-(6-Methoxychroman-3-carbonyl)-2, 2-dimethyl-l, 3-dioxane-4, 6 -dione in 72% yield. 1H-NMR (DMSO-d6, 400MHz) δ 6.68 (d, J=8.8 Hz, 1H), 6.60 (dd, J=8.8, 2.4 Hz, 1H), 6.54 (d, J=2.4 Hz, 1H), 4.38-4.32 (m, 1H), 4.27-4.25 (m, 1H), 4.14 (s, 1H), 4.12- 4.11 (m, 1H), 3.69 (s, 3H), 3.05-2.92 (m, 2H).

References: [1]Patent: WO2011/50245,2011,A1 .Location in patent: Page/Page column 116.

19
[ 182570-26-9 ]
[ 1296201-70-1 ]

References: [1]Patent: WO2011/50245,2011,A1 .

20
[ 182570-26-9 ]
[ 1296202-58-8 ]

References: [1]Patent: WO2011/50245,2011,A1 .

21
[ 182570-26-9 ]
[ 1296200-14-0 ]

References: [1]Patent: WO2011/50245,2011,A1 .

22
[ 182570-26-9 ]
methyl 2-(2-((tert-butoxycarbonyl)amino)-N-isobutylacetamido)acetate [ No CAS ]
methyl 2-(N-isobutyl-2-(6-methoxychroman-3-carbonylamino)acetamido)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		Methyl 2-(N-isobutyl-2-(6-methoxychroman-3-carboxamido)acetamido)acetate (15SY A solution of 14S (0.91 g, 3 mmol) in 30% TFA/DCM was stirred at r.t for lh. After evaporation of most TFA and DCM, toluene was applied twice to the residue to remove trace amount of TFA by evaporation in a Rotovapor. The resulting residue was added to a solution of <strong>[182570-26-9]6-methoxychroman-3-carboxylic acid</strong> (0.7 g, 3.3 mmol), EDC (0.8 g, 4 mmol), HOBt (0.5 g, 3.1 mmol), and DIEA (1.65 mL, 10 mmol) in DMF. After stirring at r.t for 2h, the suspension was poured into ethyl acetate (400 mL), washed by saturated NaHC03 solution, brine, IN HC1 solution, brine, and dried over Na2S04. The solvent was evaporated in a Rotovapor, and the residue was purified by chromatography (Combi-Flash system) using MeOH/DCM as solvents to give the titled compound 15S (0.9 g, 77%). MS calculated for C20H28N2O6 M+H: 393; observed M+H: 393.

References: [1]Patent: WO2014/200682,2014,A1 .Location in patent: Page/Page column 65-66.

23
[ 182570-26-9 ]
[ 182570-28-1 ]
(R)-6-methoxychroman-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.65 g; 39.3%	With (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol; In methanol; acetonitrile;	Raw material and solvent loading: racemic <strong>[182570-26-9]6-methoxychroman-3-carboxylic acid</strong> (1 eq, 2.80 g), dissolving agent (1R, 2R)-2-amino-1-(4 -Nitrophenyl)propane-1,3-diol (1.5 eq, 4.28g), acetonitrile (300mL), MeOH (30mL); eluted solid eluted with acetonitrile (500mL) to give (R)-6- Oxychroman-3-carboxylic acid-(1R,2R)-2-amino-1-(4-nitrophenyl)propane-1,3-diol salt 2.79 g. The organic solvent used for the extraction was ethyl acetate (100 mL) and water (100 mL). The solvent used for recrystallization was n-hexane (100 mL) and acetonitrile (10 mL). Finally, 1.10 g of (R)-<strong>[182570-26-9]6-methoxychroman-3-carboxylic acid</strong> was obtained in a yield of 39.3%, and the optical purity was 96.3%.The organic solvent used for the extraction of the recovery process was dichloromethane (300 mL).The recovered (1R, 2R)-2-amino-1-(4-nitrophenyl)propane-1,3-diol 3.58 g was recovered, and the recovery was 83.6%, and the optical purity was also 25.3%. (S)-<strong>[182570-26-9]6-methoxychroman-3-carboxylic acid</strong> 1.65 g.

References: [1]Patent: CN108503617,2018,A .Location in patent: Paragraph 0043-0047; 0049; 0050-0052.

24
[ 182570-26-9 ]
(1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol [ No CAS ]
(S)-6-methoxychroman-3-carboxylic acid (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.09 g	In methanol; acetonitrile;	Raw material and solvent loading: racemic <strong>[182570-26-9]6-methoxychroman-3-carboxylic acid</strong> (1 eq, 3.10 g), unpacking(1S,2S)-2-Amino-1-(4-nitrophenyl)propane-1,3-diol (1.5 eq, 4.74 g), acetonitrile (300 mL)Methanol (30 mL); the precipitated solid was washed with acetonitrile (500 mL) to give (S)-<strong>[182570-26-9]6-methoxychroman-3-carboxylic acid</strong>-(1S,2S)-2-amino-1-( 4-Nitrophenyl)propane-1,3-diol salt 3.09 g.The organic solvent used for the extraction was ethyl acetate (100 mL) and water (100 mL). The solvent used for recrystallization was n-hexane (100 mL) and acetonitrile (10 mL). Finally, (S)-<strong>[182570-26-9]6-methoxychroman-3-carboxylic acid</strong> 1.14g,The yield was 36.8% and the optical purity was 97.3%.

References: [1]Patent: CN108586413,2018,A .Location in patent: Paragraph 0043-0044; 0046-0047; 0050-0051.

25
[ 182570-26-9 ]
[ 99281-88-6 ]
(E)-methyl 4-(6-methoxychroman-3-carboxamido)but-2-enoate [ No CAS ]

References: [1]Journal of the American Chemical Society,2019,vol. 141,p. 2703 - 2712.

26
(E)-methyl 5-aminopent-2-enoate trifluoroacetic acid salt [ No CAS ]
[ 182570-26-9 ]
(E)-methyl 5-(6-methoxychroman-3-carboxamido)pent-2-enoate [ No CAS ]

References: [1]Journal of the American Chemical Society,2019,vol. 141,p. 2703 - 2712.

27
[ 57543-62-1 ]
[ 182570-26-9 ]