Triethylsilane → HCID 86584843, compound

HRID 1006801Notes

Reaction equation

HRID 1006801 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13]CC2C=CC(OC)=CC=2)[CH2:10][C@H:9]1[CH2:23][N:24]([CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])[CH2:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[F:33])=[O:7])[CH2:2][CH2:3][CH3:4].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH2:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([SH:13])[CH2:10][C@H:9]1[CH2:23][N:24]([CH2:34][C:35]([OH:37])=[O:36])[CH2:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[F:33])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 69429825HCID 69429825, compound

Product 1

HCID 86584843HCID 86584843, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

250 mg (0.42 mmol) (2S,4R)-2-[[tert-butoxycarbonylmethyl-(2,5-difluoro-benzyl)-amino]-methyl]-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid butyl ester were treated with 670 μl (4.2 mmol, 10 eq) triethyl silane in 7.5 ml TFA at 80° C. for 1.5 h. The solvent was evaporated and the residue was redissolved in toluene and evaporated. The crude material was purified by flash chromatography yielding 85 mg (49%) (2S,4R)-2-[[carboxymethyl-(2,5-difluoro-benzyl)-amino]-methyl]-4-mercapto-pyrrolidine-1-carboxylic acid butyl ester as light brown oil, MS: 417 (MH+).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was redissolved in toluene
  3. customevaporated
  4. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-2ce0567d8f8b4ed291bb36cefcab3c1c
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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