Triethylamine → HCID 131722442, compound

HRID 1531938Notes

Reaction equation

HRID 1531938 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH:12]1[C:22]2[CH:21]=[CH:20][C:19]3[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=3[CH:17]([C:27]3[C:28](=[O:48])[NH:29][C:30](=[O:47])[N:31]([CH2:33][C:34]4[CH:35]=[C:36]([CH2:40][NH:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])[CH:37]=[CH:38][CH:39]=4)[CH:32]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH:23]1[C:19]2[CH:20]=[CH:21][C:22]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[CH:17]([C:27]3[C:28](=[O:48])[NH:29][C:30](=[O:47])[N:31]([CH2:33][C:34]4[CH:35]=[C:36]([CH2:40][N:41]([C:2]([O:4][CH2:5][C:6]5[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=5)=[O:3])[CH2:42][C:43]([O:45][CH3:46])=[O:44])[CH:37]=[CH:38][CH:39]=4)[CH:32]=3)[C:18]=2[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 10387Benzyl chloroformate2×HCID 131722440HCID 131722440, compound

Product 1

HCID 131722442HCID 131722442, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl chloroformate (0.145 ml) was added to a solution of the product of step (iv) (0.44 g) and triethylamine (0.17 ml) in dichloromethane (10 ml). The mixture was stirred at room temperature for 2 hours. Further aliquots of benzyl chloroformate (0.1 ml) and triethylamine (0.3 ml) were added after 2 and 4 hours. The mixture was stirred overnight and partitioned between ethyl acetate and water. The organic phase was dried (MgSO4), evaporated and purified by chromatography eluting with 60% ethyl acetate in isohexane.

Workup

  1. stirringThe mixture was stirred overnight
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. custompurified by chromatography
  6. washeluting with 60% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-b6a982284e0746af825a650e5bc1aa49
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Reaction notes

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