Hydrochloric Acid → HCID 18551832, compound

HRID 1266701Notes

Reaction equation

Cl.C([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])C.[OH-].[Na+].Cl>C1COCC1>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([NH:21][CH:6]([C:7]2[CH:12]=[C:11]([O:13][CH2:14][CH3:15])[C:10]([O:16][CH2:17][CH2:18][OH:19])=[CH:9][C:8]=2[F:20])[C:5]([OH:31])=[O:4])=[CH:27][CH:26]=1)(=[NH:29])[NH2:30]

Participants

Conditions

Temperature: 0 °C

Procedure

The (RS)-(4-carbamimidoyl-phenylamino)-[5-ethoxy-2-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-acetic acid ethyl ester hydrochloride (172 mg) described in example 1.6 was suspended in THF (1.1 ml). A solution of NaOH (0.82 ml, 1 M in H2O) was added and stirred for 30 min at 0° C. and for 40 min at room temperature. 1M HCl (0.41 ml) was added. The mixture was concentrated. The solid was washed with water and ether and dried to give 129 mg of (RS)-(4-carbamimidoyl-phenylamino)-[5-ethoxy-2-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-acetic acid as a colorless solid. MS: 392 ([M+H]+).

Workup

concentrationThe mixture was concentrated
washThe solid was washed with water and ether
customdried

Sources & evidence

ORD record: ord-973c00c271ea467b81c0c8820acbb877
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548694B2

Reaction notes

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