Ethylamine → HCID 18335099, compound

HRID 842220Notes

Reaction equation

HRID 842220 reaction equation
[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([C:18]([OH:20])=O)[CH:15]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:35]([NH2:37])[CH3:36].CCN(CC)CC>C(Cl)Cl>[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([C:18]([NH:37][CH2:35][CH3:36])=[O:20])[CH:15]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[CH2:14]2)=[O:12])[C:6]2[C:5](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6341EthylamineHCID 8471TriethylamineHCID 9804299HCID 9804299, compound

Product 1

HCID 18335099HCID 18335099, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.037 g (0.08 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-carboxypyrrolidine and 0.06 mL (0.12 mmol) of ethylamine in 2 mL of CH2Cl2 at rt was added 0.031 g (0.12 mmol) of BOPCl Bis(2-oxo-3-oxazolidinyl)phosphinic chloride, Aldrich) and 0.045 mL Et3N and the reaction mixture was stirred for 18 h. The reAction mixture was concentrated and the residue was purified by chromatography (silica, acetone:hexanes, 1:2) to give the title compound. 1H NMR (CDCl3) δ (key peaks) 7.85-7.90 (m, 3H), 7.45-7.56 (m, 4H), 7.09-7.19 (m, 2H), 6.96-7.03 (m, 2H), 3.94-4.49 (m, 4H); Mass Spectrum (ESI) m/e=488 (M+1).

Workup

  1. concentrationThe reAction mixture was concentrated
  2. customthe residue was purified by chromatography (silica, acetone:hexanes, 1:2)

Sources & evidence

ORD record
ord-ea4b9adf6c394223b39e4a9122fefbe2
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

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