Formic Acid → HCID 11773543, compound

HRID 1007878Notes

Reaction equation

C(O)=O.[C:4]([O:7][C:8](=O)[CH3:9])(=[O:6])C.[C:11]([O:15][C:16](=[O:36])[NH:17][C@@H:18]([CH2:26][NH:27]OCC1C=CC=CC=1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:14])([CH3:13])[CH3:12].C([O-])(O)=O.[Na+]>ClCCl>[C:11]([O:15][C:16](=[O:36])[NH:17][C@@H:18]([CH2:26][NH:27][C:4]([O:7][CH2:8][C:9]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:26]=1)=[O:6])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:12])([CH3:13])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold mixture of formic acid (2.3 g, 73.0 mmol) and acetic anhydride (0.56 mL, 6.0 mmol) was added dropwise [(R)-1-(Benzyloxyaminomethyl)-2-phenyl-ethyl)-carbamic acid tert-butyl ester (0.20 g, 0.56 mmol) in dichloromethane (2.8 mL) at 0° C. The reaction mixture was stirred at 0° C. for 3 hours, and then treated with saturated aq. NaHCO3 (5 mL). The aqueous layer was extracted with dichloromethane (10 mL×2). The organic extracts were washed with water and brine, and dried over MgSO4. After removal of the solvent under reduced pressure, purification by flash column chromatography using an eluting system of hexane/EtOAc (2:1) yielded 0.19 g (86%) of the title compound 1H NMR (400 MHz, CDCl3): δ 8.14 (br s, 1H), 7.32-7.07 (m, 10H), 4.90-4.67 (m, 2H), 4.15 (m, 1H), 3.74 (m, 1H), 3.36 (m, 1H), 2.78 (m, 1H), 2.68 (m, 2H), 1.32 (m, 9H). MH+385.

Workup

extractionThe aqueous layer was extracted with dichloromethane (10 mL×2)
washThe organic extracts were washed with water and brine
dry with materialdried over MgSO4
customAfter removal of the solvent
customunder reduced pressure, purification by flash column chromatography

Sources & evidence

ORD record: ord-acb80ad269134542832e049926cb7f7a
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06797730B2

Reaction notes

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