Triethylamine → HCID 178472667, compound

HRID 1266717Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 8.85 g (RS)-(4-cyano-phenylamino)-[5-ethoxy-2-fluoro-3-[(R)-tetrahydro-furan-3-yloxy]-phenyl]-acetic acid ethyl ester described in example 3.6 in 515 ml EtOH were added 20.21 g hydroxylamine hydrochloride and 81.1 ml triethylamine. The solution was stirred over night at 50° C., then evaporated. The crude product was isolated by extraction with EtOAc, then purified by chromatography on silica gel (CH2Cl2/MeOH) to yield 7.64 g (RS)-[5-ethoxy-2-fluoro-3-[(R)-tetrahydro-furan-3-yloxy]-phenyl]-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetic acid ethyl ester as a light brown amorphous solid.

Workup

customevaporated
customThe crude product was isolated by extraction with EtOAc
custompurified by chromatography on silica gel (CH2Cl2/MeOH)

Sources & evidence

ORD record: ord-3b7b268995064b8a9f0becefb20742a7
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548694B2

Reaction notes

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