Formic Acid → 1-{[(Benzyloxy)(formyl)amino]methyl}cycloheptane-1-carboxylic acid

HRID 2055192Notes

Reaction equation

[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[CH2:11]([O:18][NH:19][CH2:20][C:21]1([C:28]([OH:30])=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[CH2:11]([O:18][N:19]([CH2:20][C:21]1([C:28]([OH:30])=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH:1]=[O:2])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold solution of formic acid (40.2 mL, 1.04 mol) in dichloromethane (150 mL) at 0° C. under a nitrogen atmosphere was added acetic anhydride (15.2 mL, 160 mmol). After 1 h, a solution of 1-(benzyloxyamino-methyl)-cycloheptanecarboxylic acid from Preparation 37 (16.1 mmol theoretical) in dichloromethane (150 mL) was added. The reaction was stirred at 0° C. for 3 h and was concentrated in vacuo. Water (150 mL) was added and the mixture was extracted with dichloromethane (50 mL×5). The combined organic extracts were dried (MgSO4) and were evaporated in vacuo. Purification by preparative, reverse-phase HPLC provided the title compound (2.56 g, 52%). MH+306.

Workup

additionwas added
concentrationwas concentrated in vacuo
additionWater (150 mL) was added
extractionthe mixture was extracted with dichloromethane (50 mL×5)
dry with materialThe combined organic extracts were dried (MgSO4)
customwere evaporated in vacuo
customPurification by preparative, reverse-phase HPLC

Sources & evidence

ORD record: ord-fa81cd08d19f40788e65279cb114cb93
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07332485B2

Reaction notes

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