Triethylsilane → (2S,4R)-4-Mercapto-2-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-1-carboxylic acid 2-methoxycarbonyl-phenyl ester

HRID 458352Notes

Reaction equation

HRID 458352 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]([N:14]1[CH2:18][C@H:17]([S:19]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:16][C@H:15]1[CH2:39][O:40][CH2:41][C:42]1[CH:47]=[C:46]([F:48])[C:45]([F:49])=[CH:44][C:43]=1[F:50])=[O:13])=[O:4].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]([N:14]1[CH2:18][C@H:17]([SH:19])[CH2:16][C@H:15]1[CH2:39][O:40][CH2:41][C:42]1[CH:47]=[C:46]([F:48])[C:45]([F:49])=[CH:44][C:43]=1[F:50])=[O:13])=[O:4]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 11331466(2S,4R)-2-(2,4,5-trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid 2-methoxycarbonyl-phenyl ester

Product 1

HCID 9804041(2S,4R)-4-Mercapto-2-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-1-carboxylic acid 2-methoxycarbonyl-phenyl ester

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(Method 3): A solution of 0.4 g (0.58 mmol) (2S,4R)-2-(2,4,5-trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid 2-methoxycarbonyl-phenyl ester in 5.8 ml TFA was treated at 0° C. with 0.92 ml (5.78 mmol) triethylsilane and after 10 min at room temperature evaporated and purified by flash chromatography on silica gel (Hexane/EtOAc 4:1) to give 0.22 (82%) (2S,4R)-4-mercapto-2-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-1-carboxylic acid 2-methoxycarbonyl-phenyl ester, MS: 456 (MH+).

Workup

  1. customevaporated
  2. custompurified by flash chromatography on silica gel (Hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-0413ddd2a9654ecdb42e111e1e699a13
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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