Trifluoroacetic acid → HCID 70002907, compound

HRID 1264414Notes

Reaction equation

HRID 1264414 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([S:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:33](=[O:43])[N:34]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH3:35])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:36]([N:34]([CH3:35])[C:33]([C@@H:9]1[CH2:10][C@@H:11]([S:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:12][NH:8]1)=[O:43])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70001495HCID 70001495, compound

Product 1

HCID 70002907HCID 70002907, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

19176 B73: A solution of 9.68 g (16.33 mmol) (2S,4R)-2-(Benzyl-methyl-carbamoyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester in 33 ml CH2Cl2 was treated at −20° C. with 36 ml TFA, warmed up to RT during 5.5h and kept over night at 0° C.. The reaction was evaporated and treated with aqueous saturated NaHCO3 solution/EtOAc (3×), the organic phase was dried (Na2SO4) and evaporated to give 7.59 g (95%) (2S,4R)-4-Tritylsulfanyl-pyrrolidine-2-carboxylic acid benzyl-methyl-amide, MS: 493 (MH+).

Workup

  1. waitkept over night at 0° C.
  2. customThe reaction was evaporated
  3. additiontreated with aqueous saturated NaHCO3 solution/EtOAc (3×)
  4. dry with materialthe organic phase was dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-91ce1f3b292448c38c599d6cd9ba9b4c
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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