(S)-2-fluoro-2-methyl-malonic acid monoethyl ester → HCID 69039663, compound

HRID 1372945Notes

Reaction equation

HRID 1372945 reaction equation
[NH2:1][C@@H:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]1=2.[CH2:18]([O:20][C:21](=[O:28])[C@:22]([F:27])([CH3:26])[C:23](O)=[O:24])[CH3:19]>>[CH2:18]([O:20][C:21](=[O:28])[C@:22]([F:27])([CH3:26])[C:23]([NH:1][C@@H:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]1=2)=[O:24])[CH3:19]

Participants

3

Reactant 2

HCID 13350487(S)-2-fluoro-2-methyl-malonic acid monoethyl esterHCID 25067537(7S)-7-Amino-5,7-dihydro-6H-dibenzo[b,d]azepin-6-one

Product 1

HCID 69039663HCID 69039663, compound

Procedure

In an analogous manner to that described in Example 1 a), the condensation of (S)-7-amino-5H,7H-dibenzo[b,d]azepin-6-one and (2S)-2-fluoro-2-methyl-malonic acid mono ethyl ester (96.9% e.e.) yielded the title compound as a white solid; MS: m/e=371 (M+H)+. The (2S)-2-fluoro-2-methyl-malonic acid mono ethyl ester was obtained by stereoselective hydrolysis of the corresponding diester by Candida cylindracea hydrolase following the procedure described in J. Org. Chem. 1986, 51, 1003-6.

Sources & evidence

ORD record
ord-6f38f2b948924a0ba9624930edf71c74
Source dataset
uspto-grants-2007_01
Patent number
US07160875B2

Reaction notes

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