Acetic Acid → HCID 22318856, compound

HRID 481062Notes

Reaction equation

C([O:5][C:6](=[O:32])[CH2:7][N:8]([C:20](=[O:31])[CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)(C)(C)C.O.[OH-].[Na+].C(O)(=O)C>C1COCC1>[C:27]([O:26][C:24]([NH:23][CH2:22][CH2:21][C:20]([N:8]([CH2:7][C:6]([OH:32])=[O:5])[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)=[O:31])=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of {(3-tert-Butoxycarbonylamino-propionyl)-[2-(4-nitro-phenyl)-ethyl]-amino}-acetic acid tert-butyl ester (2.5 mmol) in 11 mL THF is 22 mL water added, followed by NaOH (17.5 mmol). After heating at 60° C. for 5½ hours it is quenched with acetic acid (20 mmol). It is placed in the refrigerator for 2% days. The THF is evaporated off, and the remaining water is extracted several times with EtOAc. The organic layers are combined, dried over Na2SO4 and evaporated in vacuo yielding {(3-tert-Butoxycarbonylamino-propionyl)-[2-(4-nitro-phenyl)-ethyl]-amino}-acetic acid, 983 mg, as a dark yellow/brown oil/foam (99%): 1H NMR (CD3OD) 1.40 (d, 9H), 2.44-2.45 (m, 2H), [2.98, 3.03](t, 2H), 3.22-3.30 (m, 2H), [3.60, 3.65](t, 2H), 4.06 (s, 2H), [7.52, 7.54](d, 2h), 8.16 (t, 2H); LRMS calcd 395.42, found [M−H] 394.0.

Workup

additionadded
customThe THF is evaporated off
extractionthe remaining water is extracted several times with EtOAc
dry with materialdried over Na2SO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-cf758aacd7c3491489eb970f4081a823
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06653471B2

Reaction notes

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