Water → HCID 21356630, compound

HRID 1167427Notes

Reaction equation

HRID 1167427 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([O:6][CH2:7][C@@H:8]2[O:12][C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][OH:28])[CH2:22][CH:21]=4)=[C:16]([F:29])[CH:15]=3)[CH2:9]2)=[N:2]1.C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38].O>ClCCl>[O:1]1[CH:5]=[CH:4][C:3]([O:6][CH2:7][C@@H:8]2[O:12][C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][O:28][C:37](=[O:39])[CH3:38])[CH2:22][CH:21]=4)=[C:16]([F:29])[CH:15]=3)[CH2:9]2)=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 497382HCID 497382, compound

Product 1

HCID 21356630HCID 21356630, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Example 57(103 mg, 0.26 mmol) and triethylamine (77.4 mg, 0.77 mmol) in dichloromethane (10 ml) at 0° C. and under an atmosphere of nitrogen, was added dropwise acetyl chloride (60.2 mg, 0.77 mmol). The reaction was then allowed to warm to ambient temperature and stir for 1 hour. Water was added and the organic phase separated, washed with sat NaCl and then dried over MgSO4 and evaporated under reduced pressure. This yielded the title compound as a clear orange glass (110 mg, 97%). MS: ESP+ (M+H)+=446.

Workup

  1. customthe organic phase separated
  2. washwashed with sat NaCl
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8e813e8730ef4047b3316258ac63ec88
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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