1-Phenylcyclopropanemethanamine → 5-hydroxy-8-{1-hydroxy-2-[(1-phenyl-cyclopropylmethyl)-amino]-ethyl}-4H-benzo[1,4]oxazin-3-one

HRID 29846노트

반응식

C([O:8][C:9]1[C:14]2[NH:15][C:16](=[O:19])[CH2:17][O:18][C:13]=2[C:12]([C:20](=[O:24])[CH:21](O)O)=[CH:11][CH:10]=1)C1C=CC=CC=1.[C:25]1([C:31]2([CH2:34][NH2:35])[CH2:33][CH2:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[OH:8][C:9]1[C:14]2[NH:15][C:16](=[O:19])[CH2:17][O:18][C:13]=2[C:12]([CH:20]([OH:24])[CH2:21][NH:35][CH2:34][C:31]2([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:33][CH2:32]2)=[CH:11][CH:10]=1

참가 물질

반응물 2

HCID 702871-Phenylcyclopropanemethanamine

HCID 231061485-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one

생성물 1

HCID 115086535-hydroxy-8-{1-hydroxy-2-[(1-phenyl-cyclopropylmethyl)-amino]-ethyl}-4H-benzo[1,4]oxazin-3-one

실험 절차

Prepared from 329 mg (1 mmol) 5-benzyloxy-8-(2,2-dihydroxy-acetyl)-4H-benzo[1,4]oxazin-3-one and 147 mg (1 mmol) C-(1-phenyl-cyclopropyl)-methylamine. Final purification by chromatography (silica gel; dichloromethane/methanol gradient). Yield: 30 mg (8%); mass spectroscopy: [M+H]+=355.

후처리

customFinal purification by chromatography (silica gel; dichloromethane/methanol gradient)

출처 및 근거

ORD 기록: ord-d5d372f59c294a2093a33b43d5fb4233
출처 데이터셋: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07423035B2

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