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Quality Control of 5-(tert-Butoxy)-5-oxopentanoic acid Purity: 95% SDS Specification

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Product Details of 5-(tert-Butoxy)-5-oxopentanoic acid

CAS No. :	63128-51-8
Formula :	C₉H₁₆O₄
M.W :	188.22
SMILES Code :	O=C(O)CCCC(OC(C)(C)C)=O
MDL No. :	MFCD09759103
InChI Key :	VZHNAVSRNGLHRD-UHFFFAOYSA-N
Pubchem ID :	11424021

Safety of 5-(tert-Butoxy)-5-oxopentanoic acid

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H318
Precautionary Statements:	P280-P305+P351+P338
Class:	8
UN#:	3265
Packing Group:	Ⅱ

Application In Synthesis of 5-(tert-Butoxy)-5-oxopentanoic acid

* 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 [ 63128-51-8 ]

[ 63128-51-8 ] Synthesis Path-Downstream 1~35

1
[ 63128-51-8 ]
[ 110-94-1 ]
[ 115-11-7 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1944,vol. 63,p. 189.

2
[ 1070-62-8 ]
[ 75-65-0 ]
[ 63128-51-8 ]

References: [1]Justus Liebigs Annalen der Chemie,1977,vol. No.6,p. 897 - 903.

3
[ 64-69-7 ]
[ 1663-39-4 ]
[ 63128-51-8 ]

References: [1]Tetrahedron,1993,vol. 49,p. 8465 - 8470.

4
[ 108-55-4 ]
[ 75-65-0 ]
[ 63128-51-8 ]

Yield	Reaction Conditions	Operation in experiment
46%	With zinc(II) chloride; at 60℃;Inert atmosphere;	ZnCl2 (4.77 mmol, 0.65 g) and glutaric anhydride (30.93 mmol, 3.53 g) were added to dried and freshly distilled tert-butyl alcohol (186 mmol, 17.8 mL) under an argon atmosphere. The reaction mixture was stirred at 60C overnight and then poured into saturated aqueous solution of NaHCO3 (60 mL) and washed with CH2Cl2 (2x40 mL). The aqueous phase was acidified with conc. H2SO4 (pH = 1) and extracted with CH2Cl2 (3 x 50 mL). The combined organic phases were washed with brine (15 mL), dried over Na2SO4 and concentrated give 5-tert-butoxy-5-oxopentanoic acid (2.67 g, 46%) as a colourless oil; 1H NMR (CDCl3): delta = 1.45 (s, 3H), 1.92 (m, 2H), 2.31 (t, J = 7.5 Hz, 2H), 2.42 (t, J = 7.5 Hz, 2H).
27%	With dmap; 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; In toluene; at 20℃; for 8.5h;	A mixture of glutaric anhydride (10 g, 87.6 mmol), N-hydroxysuccinimide (3 g, 2.1 mmol), 4-dimethylaminopyridine (1.07 g, 8.8 mmol), anhydrous tert-butanol (24 mL, 262 mmol), and triethylamine (3.6 mL, 25.8 mmol) in dry toluene was mixed at room temperature for 30 min, then boiled for 8 hours, and allowed to stand over night at room temperature. The mixture was diluted with ethyl acetate (250 mL), washed with a 10% solution of citric acid (3×100 mL), then with a saturated salt solution (2×50 mL), and dried over anhydrous sodium sulfate, and the solvent was removed under vacuum. The product was isolated by flash chromatography on silica gel with an elution mixture of ethyl acetate-hexane (1:1). The yield of ether (1) in the form of colorless oil was 4.5 g (27%), [M+H]+=187.49.

References: [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 1501 - 1510.
[2]Tetrahedron,2015,vol. 71,p. 8871 - 8875.
[3]Chemistry - A European Journal,2020.
[4]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055.
[5]Patent: US2017/183318,2017,A1 .Location in patent: Paragraph 0207; 0208.
[6]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560.
[7]Journal of Medicinal Chemistry,2019,vol. 62,p. 6597 - 6614.

5
[ 63128-51-8 ]
[ 6638-79-5 ]
[ 192123-40-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 2h;	EXAMPLE 40; Weinreb amide S2[00250] Weinreb amide S2: Prepared by a modification of a literature method. The starting carboxylic acid Sl (4.4 g, 23.4 mmol) was dissolved in CH2Cl2 (100 mL). N,O- dimethylhydroxylamineetaCl (2.51 g, 25.7 mmol), 1-hydroxybenzotriazole hydrate (3.93 g, <n="53"/>25.7 mmol), diisopropylethylamine (9.0 mL, 51.7 mmol), and EDCetaC1 (4.93 g, 25.7 mmol) were added sequentially to the reaction mixture. The solution was allowed to stir at room temperature for 2 h and then concentrated under vacuum to remove most of the CH2CI2. The crude material was diluted with EtOAc (300 mL), and washed successively with 5% aqueous NaHSO4 (3x), 5% aqueous NaHCtheta3 (3x), and brine. The organic layer was dried over MgSO4, filtered and concentrated to afford 5.14 g (95% yield) of the product as a pale yellow oil which was used without further purification. TLC Rf = 0.44 (EtOAc/hexanes, v/v, 1:2). 1HNMR (300MHz, CDCl3) delta 3.68 (s, 3H), 3.18 (s, 3H), 2.48 (t, J= 7.4 Hz, 2H), 2.30 (t, J = 7.4 Hz, 2H), 1.92 (m, 2H), 1.45 (s, 9H), FIG. 57. 13CNMR (75 MHz, CDCl3) delta 174.0, 172.7, 80.2, 77.5, 61.3, 35.0, 32.3, 31.0, 28.2, 20.2, FIG. 58. ESI-TOF-MS: [M+H]+ calculated 232.2, found 232.4.

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055.
[2]Patent: WO2007/112358,2007,A1 .Location in patent: Page/Page column 51-52.
[3]Journal of the Chemical Society. Perkin transactions I,1997,p. 1501 - 1510.
[4]Journal of the Chemical Society. Perkin transactions I,1997,p. 1501 - 1510.

6
[ 63128-51-8 ]
[ 126-81-8 ]
[ 208648-73-1 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 2189 - 2192.
[2]Tetrahedron Letters,1998,vol. 39,p. 3585 - 3588.

9
[ 43052-39-7 ]
alkali [ No CAS ]
aqueous dioxane [ No CAS ]
[ 63128-51-8 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1944,vol. 63,p. 189.

10
di-tert-butyl glutarate [ No CAS ]
[ 63128-51-8 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1939,vol. 58,p. 1058.

11
[ 63128-51-8 ]
[ 191090-32-1 ]
[ 637337-54-3 ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560.

12
[ 41355-50-4 ]
[ 63128-51-8 ]
[ 902760-42-3 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 4775 - 4780.

13
[ 53715-97-2 ]
[ 75-65-0 ]
[ 63128-51-8 ]

Yield	Reaction Conditions	Operation in experiment
27%	With dmap; 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; In toluene; at 115℃; for 16h;	EXAMPLE 39; Carboxylic acid SlO O>k O ^ ^ OH S1[00248] Carboxylic acid Sl: Prepared as previously described in the literature. Glutaric anhydride (10.0 g, 87.6 mmol) was weighed into a dry flask and purged with N2. Dry toluene (50 mL) was added followed by N-hydroxysuccinimide (3.0 g, 26.1 mmol), 4- dimethylaminopyridine (1.07 g, 8.8 mmol), anhydrous tert-butanol (24.3 mL, 262.3 mmol), and triethylamine (3.6 ml, 25.8 mmol). The flask was fitted with a reflux condenser, heated to 115C, and allowed to stir for 16 h under N2. The solution was cooled to room temperature, diluted with 300 mL EtOAc, and washed with 5% aqueous NaHSO4 (3x) followed by brine. The organic layer was dried over MgSO4, filtered and concentrated. The crude material was purified by chromatography eluting with 1: 1 hexanes/EtOAc to yield 4.48 g (27% yield) of the product as a colorless oil. TLC Rf = 0.34 (EtOAc/hexanes, v/v, 1 : 1). 1HNMR (300MHz, CDCl3): delta 10.83 (br s, IH), 2.42 (t, J= 7.4 Hz, 2H), 2.31 (t, J= 2.31 Hz, 2H), 1.92 (m, 2H), 1.45 (s, 9H). FIG. 55. 13CNMR (75 MHz, CDCl3): delta 179.2, 172.3, 80.5, 34.4, 33.0, 28.0, 20.0. FIG. 56. ESI-TOF-MS: [M-H]" calculated 187.1, found 187.4.

References: [1]Patent: WO2007/112358,2007,A1 .Location in patent: Page/Page column 51.

14
[ 63128-51-8 ]
C₂₅H₃₃NO₃ [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055.

15
[ 63128-51-8 ]
[ 941292-97-3 ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055.

16
[ 63128-51-8 ]
(R)-β-carboxyethyl-tert-butyl ester-γ-(S)-N-benzyl-α-methylbenzyl amino-propylalcohol [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055.

17
[ 63128-51-8 ]
C₁₀H₂₁NO₃ [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055.

18
[ 63128-51-8 ]
[ 941292-98-4 ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055.

19
[ 63128-51-8 ]
[ 192123-41-4 ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055.
[2]Journal of the Chemical Society. Perkin transactions I,1997,p. 1501 - 1510.
[3]Journal of Medicinal Chemistry,2019,vol. 62,p. 6597 - 6614.

20
[ 63128-51-8 ]
(S)-2-[(9H-fluoren-9-ylmethoxycarbonyl)aminomethyl]-pentanedioic acid 5-tert-butyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055.
[2]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560.

21
[ 63128-51-8 ]
[ 637337-13-4 ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560.

22
[ 63128-51-8 ]
2-aminomethyl-pentanedioic acid 5-tert-butyl ester [ No CAS ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560.

23
[ 63128-51-8 ]
[ 637337-69-0 ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560.

24
[ 63128-51-8 ]
(S)-2-(Benzyloxycarbonylamino-methyl)-pentanedioic acid 1-benzyl ester [ No CAS ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560.

25
[ 63128-51-8 ]
H-(S)β²hGln(Trt)-OH [ No CAS ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560.

26
[ 63128-51-8 ]
[ 756531-84-7 ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560.

27
[ 63128-51-8 ]
[ 756531-82-5 ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560.

28
[ 63128-51-8 ]
[ 756531-77-8 ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560.

29
[ 63128-51-8 ]
[ 756531-78-9 ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560.

30
[ 63128-51-8 ]
[ 756531-86-9 ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560.

31
[ 63128-51-8 ]
2-[(9H-fluoren-9-ylmethoxycarbonylamino)-methyl]-4-(trityl-carbamoyl)-butyric acid [ No CAS ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560.

32
[ 63128-51-8 ]
[ 208648-74-2 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 2189 - 2192.

33
[ 63128-51-8 ]
[ 338958-01-3 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 2189 - 2192.

34
[ 63128-51-8 ]
2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentanoic acid 4-[4-carboxy-1-(4,4-dimethyl-2,6-dioxo-cyclohexylidene)-butylamino]-benzyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 2189 - 2192.

35
[ 63128-51-8 ]
tert-butyl 5-(4-(N-9-fluorenylmethoxycarbonylleucinyl-oxymethyl)anilino)-5-(4,4-dimethylcyclohexylidene-2,6-dioxo)pentanoate [ No CAS ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 2189 - 2192.

Historical Records

Technical Information

• Arndt-Eistert Homologation • Hunsdiecker-Borodin Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Ugi Reaction

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H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 63128-51-8

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CAS No.: 63128-51-8

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[ 63128-51-8 ] Synthesis Path-Downstream 1~35

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