Ethyl orthoformate → HCID 58564203, compound

HRID 473937Notes

Reaction equation

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

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 668580744-{(S)-1-[(S)-6-(2-Hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-benzoic acid hydrazide

Product 1

HCID 58564203HCID 58564203, compound

Conditions

Temperature: 90 °C

Procedure

4-{(S)-1-[(S)-6-(2-Hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-benzoic acid hydrazide (300 mg) taken up in triethyl orthoformate (2.5 mL) was stirred at 90° C. for 3 h. After cooling to ambient temperature, the mixture was purified by chromatography on silica gel (CH2Cl2/MeOH 99:1->97:3) to afford the title compound.

Workup

temperatureAfter cooling to ambient temperature
customthe mixture was purified by chromatography on silica gel (CH2Cl2/MeOH 99:1->97:3)

Sources & evidence

ORD record: ord-195ebbe54659497f844fde06874ab8a3
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637505B2

Reaction notes

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