Triethylamine → HCID 178472630, compound

HRID 840788Notes

Reaction equation

HRID 840788 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][N:6]1[CH2:11][CH2:10][NH:9][C@@H:8]([CH2:12][CH2:13][C:14]([NH:16][CH2:17][NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[NH:15])[C:7]1=[O:29])[CH3:2].[CH2:31]([O:38][C:39](ON1C(=O)CCC1=O)=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:39]([O:38][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:40])[C@@H:8]([CH2:12][CH2:13][C:14]([NH:16][CH2:17][NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)(=[O:20])=[O:21])=[NH:15])[C:7]1=[O:29])=[O:30])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 178472622HCID 178472622, compound

Product 1

HCID 178472630HCID 178472630, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the compound of Example 10 (0.43 mmol), N-(benzyloxycarbonyloxy)succinimide (107 mg, 0.43 mmol) and triethylamine (0.24 mL, 1.72 mmol) in DMF (3 mL) was stirred at room temperature overnight. The mixture was diluted with ethyl acetate and the organic layer was washed with water three times, dried over anhydrous Na2SO4, filtered and evaporated to give the title compound (195 mg).

Workup

  1. washthe organic layer was washed with water three times
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-9b3f928b713f4701b0712b330b04d45a
Source dataset
uspto-grants-2002_04
Patent number
US06369063B1

Reaction notes

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