Trifluoroacetic acid → (S)-2-Amino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic Acid Tert-butyl Ester

HRID 660635Notes

Reaction equation

HRID 660635 reaction equation
[C:1]([O:5][C:6](=[O:45])[C@@H:7]([NH:37]C(OC(C)(C)C)=O)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][C:18](=[O:20])[N:17]([CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[S:16]2(=[O:28])=[O:27])=[C:11]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:45])[C@@H:7]([NH2:37])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][C:18](=[O:20])[N:17]([CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[S:16]2(=[O:27])=[O:28])=[C:11]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68840018(S)-3-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-2-tert-butoxycarbonylaminopropionic Acid Tert-butyl Ester

Product 1

HCID 68839983(S)-2-Amino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic Acid Tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-2-tert-butoxycarbonylaminopropionic acid tert-butyl ester (760 mg, 1.15 mmol) in methylene chloride (10 mL) is added TFA (3 mL) and the mixture is stirred at RT for 45 min. The solution is carefully poured into 8% NaHCO3 solution (50 mL) and the mixture is extracted with methylene chloride. The solvent is removed under reduced pressure to give the title compound which is used immediately in the next step.

Workup

  1. extractionthe mixture is extracted with methylene chloride
  2. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-57626486ce3542e9bc2304ba12912ac0
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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