Triethylamine → HCID 19787865, compound

HRID 1656537Notes

Reaction equation

HRID 1656537 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:30]([CH3:32])[CH3:31])[CH:24]([OH:29])[C:25]([F:28])([F:27])[F:26])=[O:21])[C:15]([C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:45](Cl)(=[O:50])[C:46]([CH3:49])([CH3:48])[CH3:47]>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:30]([CH3:31])[CH3:32])[CH:24]([O:29][C:45](=[O:50])[C:46]([CH3:49])([CH3:48])[CH3:47])[C:25]([F:26])([F:27])[F:28])=[O:21])[C:15]([C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 19787894HCID 19787894, compound

Product 1

HCID 19787865HCID 19787865, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[5-benzyloxycarbonylamino-6-oxo-2-(2-thienyl)-1,6-dihydro-1-pyrimidinyl]-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide (1.95 g), triethylamine (1.4 mL), and 4-dimethylaminopyridine (10 mg) in dichloromethane (35 mL) was added pivaloyl chloride (0.53 mL); and the resulting solution allowed to stir for 2 h. The solution was diluted with ethyl acetate, washed (saturated aqueous sodium bicarbonate (twice), saturated aqueous ammonium chloride, and brine), dried, and evaporated. Purification by chromatography, eluting with ethyl acetate:dichloromethane (10:90), afforded the ester (1.80 g) as a white foam; TLC: Rf =0.34, ethyl acetate:dichloromethane (10:90); MS: m/z=623(M+1).

Workup

  1. washwashed (saturated aqueous sodium bicarbonate (twice), saturated aqueous ammonium chloride, and brine),
  2. customdried
  3. customevaporated
  4. customPurification by chromatography
  5. washeluting with ethyl acetate:dichloromethane (10:90)

Sources & evidence

ORD record
ord-197ad59c0ca549788c540c553e43b1a1
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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