Trifluoroacetic acid → (3R,5S)-1-pyrimidin-2-yl-5-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-3-thiol trifluoro-acetate

HRID 431826Notes

Reaction equation

HRID 431826 reaction equation
[F:1][C:2]1[CH:41]=[C:40]([F:42])[C:39]([F:43])=[CH:38][C:3]=1[CH2:4][O:5][CH2:6][C@@H:7]1[CH2:11][C@@H:10]([S:12]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:9][N:8]1[C:32]1[N:37]=[CH:36][CH:35]=[CH:34][N:33]=1.[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45].C([SiH](C(C)C)C(C)C)(C)C>C(Cl)Cl>[F:47][C:46]([F:49])([F:48])[C:44]([OH:50])=[O:45].[N:33]1[CH:34]=[CH:35][CH:36]=[N:37][C:32]=1[N:8]1[C@H:7]([CH2:6][O:5][CH2:4][C:3]2[CH:38]=[C:39]([F:43])[C:40]([F:42])=[CH:41][C:2]=2[F:1])[CH2:11][C@@H:10]([SH:12])[CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 138754Silane, tris(1-methylethyl)-HCID 70035536(2S,4R)-2-[2-(2,4,5-Trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-pyrimidine

Product 1

HCID 9956301(3R,5S)-1-pyrimidin-2-yl-5-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-3-thiol trifluoro-acetateYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.7 g (2.84 mmol) (2S,4R)-2-[2-(2,4,5-Trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-pyrimidine in 30 ml CH2Cl2 was treated at 0° C. with 8 ml TFA and 5.82 ml (28 mmol) triisopropylsilane. After 30 min at RT the solution was completely evaporated and the compound precipitated twice from Et2O/pentane to give 1.06 g (80%) (3R,5S)-1-pyrimidin-2-yl-5-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-3-thiol trifluoro-acetate (1:1) as colourless oil, MS: 356 (MH+).

Workup

  1. customAfter 30 min at RT the solution was completely evaporated
  2. customthe compound precipitated twice from Et2O/pentane

Sources & evidence

ORD record
ord-0d29215d6e7648f4a73a2c08bf5003b6
Source dataset
uspto-grants-2003_12
Patent number
US06660738B2

Reaction notes

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