Triethylamine → HCID 19838835, compound

HRID 1639261Notes

Reaction equation

HRID 1639261 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([OH:10])=O.ClC(OCC(C)C)=O.C(N(CC)CC)C.[NH2:26][CH2:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([C:36]([NH2:38])=[O:37])[CH2:32][CH2:31]1)=[O:29]>O1CCCC1>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([NH:26][CH2:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([C:36]([NH2:38])=[O:37])[CH2:32][CH2:31]1)=[O:29])=[O:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 31466872-(2-Oxopyrrolidin-1-yl)acetic acidHCID 19838833HCID 19838833, compound

Product 1

HCID 19838835HCID 19838835, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

27.8 g of (2-oxo-1-pyrrolidinyl)acetic acid was suspended in 450 ml of tetrahydrofuran, to which 27.8 g of isobutyl chloroformate at -15° C. and 20.3 g of triethylamine at -15° to -5° C. were added. After stirring at -10° to -5° C. for 15 minutes, 36.0 g of 1-glycyl-4-piperidinecarboxamide was added at -10° to -5° C. and then the reaction liquid was allowed to stand so as to rise its temperature to room temperature over 2 hours. The insoluble matter was filtered off and suspended in 500 ml of chloroform. The suspension was filtered off to obtain the crude crystal. The crude crystal was recrystallized from methanol to obtain the titled compound.

Workup

  1. customthe reaction liquid
  2. customto room temperature
  3. customover 2 hours
  4. filtrationThe insoluble matter was filtered off
  5. filtrationThe suspension was filtered off
  6. customto obtain the crude crystal
  7. customThe crude crystal was recrystallized from methanol

Sources & evidence

ORD record
ord-41e62616d74f4fe5ba8a155153eb4ee5
Source dataset
uspto-grants-1989_11
Patent number
US04883802

Reaction notes

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