(2R)-Oxiran-2-ylmethyl butanoate → HCID 57526976, compound

HRID 1452566Notes

Reaction equation

HRID 1452566 reaction equation
C(O[C:9](=O)[NH:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([N:18]2[CH2:23][CH2:22][S:21][CH2:20][CH2:19]2)=[C:13]([F:24])[CH:12]=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:36]([O:41][CH2:42][C@@H:43]1[O:45]C1)(=[O:40])CCC>>[F:17][C:15]1[CH:16]=[C:11]([N:10]2[CH2:9][C@H:42]([CH2:43][OH:45])[O:41][C:36]2=[O:40])[CH:12]=[C:13]([F:24])[C:14]=1[N:18]1[CH2:19][CH2:20][S:21][CH2:22][CH2:23]1

Participants

4

Reactant 3

HCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 2733832Lithium HexamethyldisilazideHCID 12096593HCID 12096593, compound

Product 1

HCID 57526976HCID 57526976, compoundYield 73.7%

Procedure

N-(3,5-Difluoro-4-thiomorpholin-4-yl-phenyl)-carbamic acid benzyl ester (WO 0232857 A1; WO 0198297 A2) (31.5 g, 86.4 mmol), lithium biS(trimethylsilyl)amide solution (95 ml, 1 M in THF) and (R)-(−)-glycidyl butyrate (14.5 g, 79.7 mmol) were reacted as described for Intermediate 25 to give the crude title compound (19.4 g).

Sources & evidence

ORD record
ord-c0e8bebb1d724131887b738f343d14d9
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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