2,2,2-Trifluoroethanol → HCID 513929, compound

HRID 987943Notes

Reaction equation

HRID 987943 reaction equation
[NH2:1][C@@H:2]([CH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1)[C:3]([NH:5][CH2:6][CH2:7][CH2:8][C@H:9]([N:12]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:10][OH:11])=[O:4].[F:38][C:39]([F:53])([F:52])[CH2:40][O:41][C:42](=O)[O:43]N1C(=O)CCC1=O.FC(F)(F)CO.C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)C(=O)C1>C([O-])([O-])=O.[K+].[K+].C1COCC1.C(OCC)(=O)C.C(N(CC)CC)C>[F:38][C:39]([F:53])([F:52])[CH2:40][O:41][C:42](=[O:43])[NH:1][C@H:2]([C:3](=[O:4])[NH:5][CH2:6][CH2:7][CH2:8][C@H:9]([N:12]([S:17]([C:20]1[CH:21]=[CH:22][C:23]([NH2:26])=[CH:24][CH:25]=1)(=[O:19])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:10][OH:11])[CH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1

Participants

9

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 513930HCID 513930, compoundHCID 676246Di(succinimido) carbonateHCID 85873330HCID 85873330, compound

Product 1

HCID 513929HCID 513929, compound

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a stirred solution of (2S,4S)-2-amino-N-{4-[(4-amino-benzenesulfonyl)-isobutyl-amino]-5-hydroxy-pentyl}-3-naphthalen-1-yl-propionamide (0.09 g, 0.17 mmol, product of example 8) in K2CO3 1M (3 mL) and THF (1 mL) was added carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 2,2,2-trifluoroethyl ester (0.05 g, 0.20 mmol), prepared from 2,2,2-trifluoroethanol, N,N′-disuccinimidyl carbonate and triethylamine in tetrahydrofuran. The mixture was stirred to room temperature for 24 h. Ethyl acetate was added and the organic layer was washed with water, then dried with MgSO4 and concentrated. The residue was purified by flash chromatography eluting with a mixture of hexane/EtOAc. The yield obtained was 10%.

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography
  5. washeluting with a mixture of hexane/EtOAc
  6. customThe yield obtained

Sources & evidence

ORD record
ord-b1446caa3194486b8ed22a52c23c1357
Source dataset
uspto-grants-2003_10
Patent number
US06632816B1

Reaction notes

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