Hydroxylamine → HCID 11855872, compound

HRID 736773Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH:12]2[CH2:13][CH2:14][CH:9]1[CH:10]([C:38]([OH:40])=O)[CH:11]2[NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:30]=[C:29]([CH3:37])[CH:28]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:41][OH:42]>>[OH:42][NH:41][C:38]([CH:10]1[CH:11]([NH:15][S:16]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[C:29]([CH3:37])[CH:28]=3)=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH:12]2[N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH:9]1[CH2:14][CH2:13]2)=[O:40]

Participants

Reactant 2

HCID 787Hydroxylamine

HCID 68819139HCID 68819139, compound

Product 1

HCID 11855872HCID 11855872, compound

Procedure

According to the procedure of Example 24, Step 3, 0.15 g (0.26 mmol) of 3-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-7-aza-bicyclo[2.2.1]heptane-2,7-dicarboxylic acid 7-tert-butyl ester and hydroxylamine gave tert-butyl 2-[(hydroxyamino)carbonyl]-3-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]-7-azabicyclo[2.2.1]heptane-7-carboxylate as an amorphous off yellow solid (0.0162 g, 14.7%) after Biotage Flash 40S chromatography, eluting with 5% methanol in ethyl acetate. MS: 583 (M+H)+

Sources & evidence

ORD record: ord-dd62599ac1ea4f7e929f3a79fabfc2f4
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Reaction notes

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