Triethylamine → HCID 70002264, compound

HRID 1266703Notes

Reaction equation

HRID 1266703 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:31])[CH:6]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[NH:30])[NH2:29])=[CH:24][CH:23]=1)[C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH3:15])[C:10]([O:16][CH2:17][CH2:18][OH:19])=[CH:9][C:8]=1[F:20])[CH3:3].Cl[C:33]([O:35][CH2:36][CH3:37])=[O:34].C(N(CC)CC)C.C(Cl)Cl.CC(C)=O>CN(C=O)C>[CH2:2]([O:4][C:5](=[O:31])[CH:6]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([NH2:29])=[N:30][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:24][CH:23]=1)[C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH3:15])[C:10]([O:16][CH2:17][CH2:18][OH:19])=[CH:9][C:8]=1[F:20])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 21584124Propan-2-one--dichloromethane (1/1)HCID 70002371HCID 70002371, compound

Product 1

HCID 70002264HCID 70002264, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The (RS)-(4-carbamimidoyl-phenylamino)-[5-ethoxy-2-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-acetic acid ethyl ester hydrochloride (100 mg) described in example 1.6 was dissolved in DMF (1 ml). At 0° C., ethyl chloroformate (24 mg) and triethylamine (67 mg) were added. The mixture was stirred for 1 h at 0° C. The product was isolated by extraction and column chromatography (CH2Cl2/acetone) to give 106 mg of (RS)-[4-(amino-ethoxycarbonylimino-methyl)-phenylamino]-[5-ethoxy-2-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-acetic acid ethyl ester as a colorless foam. MS: 492 ([M+H]+).

Sources & evidence

ORD record
ord-642dc75093c44f408a5ce2f59254fc52
Source dataset
uspto-grants-2003_04
Patent number
US06548694B2

Reaction notes

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