Triethylamine → (3-Cyano-5-oxo-6-phenyl-hexahydro-pyrrolo[2,1-b]thiazol-6-yl)-carbamic acid tert-butyl ester

HRID 507442Notes

Reaction equation

HRID 507442 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15](=[O:16])[N:14]2[CH:10]([S:11][CH2:12][CH:13]2[C:17](=O)[NH2:18])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.CCN(CC)CC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:15](=[O:16])[N:14]2[CH:10]([S:11][CH2:12][CH:13]2[C:17]#[N:18])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 68466014HCID 68466014, compound

Product 1

HCID 57443731(3-Cyano-5-oxo-6-phenyl-hexahydro-pyrrolo[2,1-b]thiazol-6-yl)-carbamic acid tert-butyl esterYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 17 (380 mg, 1.0 mmol) in CH2Cl2 (50 mL) was added TFAA (252 uL, 1.2 mmol) dropwise at room temperature, followed by the addition of Et3N (404 mg, 4 mmol). After stirring for 1 h, the mixture was washed with brine, dried over Na2SO4. After concentration, the residue was purified by column chromatography on silica gel (PE: EA=15:1) to give compound 18 (300 mg, 83.6%). 1 H NMR (400 MHz, CDCl3) δ 1.40 (s, 9 H), 3.26-3.27 (m, 1 H), 3.30-3.31 (m, 1 H), 3.31-3.34 (m, 1 H), 3.43-3.47 (m, 1 H), 5.06 (bs, 1 H), 5.22 (bs, 1H), 5.50 (bs, 1H), 7.37-7.49 (m, 5H). MS (M+1): 360.

Workup

  1. washthe mixture was washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationAfter concentration
  4. customthe residue was purified by column chromatography on silica gel (PE: EA=15:1)

Sources & evidence

ORD record
ord-bff966e037a74ae699d0d5493770a69a
Source dataset
uspto-grants-2010_08
Patent number
US07786163B2

Reaction notes

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