Methanol → HCID 53924910, compound

HRID 2185435Notes

Reaction equation

O.[OH-].[Li+].C[O:5][C:6](=[O:32])[C@@H:7]1[CH2:11][C@@H:10]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][N:8]1[C:20](=[O:31])[CH2:21][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH3:23].CO>O.O1CCCC1>[C:16]([O:15][C:13]([NH:12][C@H:10]1[CH2:9][N:8]([C:20](=[O:31])[CH2:21][N:22]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH3:23])[C@H:7]([C:6]([OH:32])=[O:5])[CH2:11]1)=[O:14])([CH3:17])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of lithium hydroxide monohydrate (35 mg) in water (2 mL) was added to a solution of trans-4-(N-tert-butoxycarbonylamino)-1-(N-tert-butoxycarbonyl-N-methylglycyl)-L-proline methyl ester (E, 289 mg) in tetrahydrofuran (6 mL)-methanol (2 mL) at 0° C. After stirring at 0° C. for 10 min and at room temperature for 15 hr, the solvents were removed in vacuo. The residue was diluted with water and washed with diethyl ether. The aqueous layer was acidified with 1 N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to afford the title compound (258 mg) as a colorless oil. The compound appears as a mixture of rotamers: 1H NMR (400 MHz, CDCl3) δ 1.36 (s, 9H), 1.38 (s, 9H), 2.03-2.30 (m, 1.5H), 2.62-2.94 (m, 3.5H), 3.20-4.02 (m, 4H), 4.07-4.42 (m, 1H), 4.46-4.62 (m 1H), 5.24-5.62 (m, 0.5H), 5.70-5.82 (m, 0.5H), and 8.60 (br s, 1H).

Workup

customthe solvents were removed in vacuo
additionThe residue was diluted with water
washwashed with diethyl ether
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-c747cd4861a0421fb6d6606e0b02871c
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06399629B1

Reaction notes

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