(2R)-Oxiran-2-ylmethyl butanoate → HCID 53833784, compound

HRID 1417951Notes

Reaction equation

HRID 1417951 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](OCC2C=CC=CC=2)=O)[CH:5]=[CH:4][C:3]=1[N:19]1[CH2:23][CH2:22][S:21][CH2:20]1.C([Li])CCC.[CH2:29]([O:33][C:34](=[O:38])CCC)[C@@H:30]1[O:32]C1>>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:9][C@H:29]([CH2:30][OH:32])[O:33][C:34]2=[O:38])[CH:5]=[CH:4][C:3]=1[N:19]1[CH2:23][CH2:22][S:21][CH2:20]1

Participants

4

Reactant 3

HCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 57053099Carbamic acid, [3-fluoro-4-(3-thiazolidinyl)phenyl]-, phenylmethyl esterHCID 178418339Butyllithium

Product 1

HCID 53833784HCID 53833784, compoundYield 78%

Procedure

Using the same general procedure as step 3 of example 1, 3-[2-fluoro-4-(benzyloxycarbonyl) aminophenyl]thiazolidine (692 mg, 2.24 mmol) was treated sequentially with n-butyllitium (1.5 mL, 2.40 mmol) and (R)--(-)-glycidylbutyrate (0.33 mL, 2.33 mmol) to provide 500 mg (78%) of the title compound. Recystallization from methylene chloridelhexane provided an analytical sample with a melting point of 96°-97° C.

Sources & evidence

ORD record
ord-b4753521ed8e405fab7e20bd8c293c93
Source dataset
uspto-grants-1999_03
Patent number
US05880118

Reaction notes

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