Hydrogen Peroxide → Ethyl 2-(tert-butoxycarbonylamino)-2-carbamoyl-3-[(-)-menthyloxycarbonyl]propionate

HRID 426025Notes

Reaction equation

C(=O)([O-])[O-:2].[K+].[K+].[C:7]([O:11][C:12]([NH:14][C:15]([C:35]#[N:36])([CH2:21][C:22]([O:24][CH:25]1[CH:30]([CH:31]([CH3:33])[CH3:32])[CH2:29][CH2:28][CH:27]([CH3:34])[CH2:26]1)=[O:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8].OO>O.CC(C)=O>[C:7]([O:11][C:12]([NH:14][C:15]([C:35](=[O:2])[NH2:36])([CH2:21][C:22]([O:24][CH:25]1[CH:30]([CH:31]([CH3:32])[CH3:33])[CH2:29][CH2:28][CH:27]([CH3:34])[CH2:26]1)=[O:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:13])([CH3:8])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 20 °C

Procedure

Potassium carbonate (586 mg, 4.24 mmol), water (2.5 ml), ethyl 2-(tert-butoxycarbonylamino)-2-cyano-3-[(−)-menthyloxycarbonyl]propionate (1.00 g, 2.46 mmol) and acetone (5 ml) were mixed and 30% aqueous hydrogen peroxide solution (0.8 ml) was added dropwise under cooling with water. Then the mixture was heated at 10-30° C. of inner temperature and stirred for about 4 hours. The precipitated crystals were filtered and washed with sprayed water. It was dried in airflow at 60° C. overnight to give ethyl 2-(tert-butoxycarbonylamino)-2-carbamoyl-3-[(−)-menthyloxycarbonyl]propionate (802 mg, yield 73.3%). Optical purity was 10.7% d.e.

Workup

filtrationThe precipitated crystals were filtered
washwashed with sprayed water
customIt was dried in airflow at 60° C. overnight

Sources & evidence

ORD record: ord-143878f5362b438795029e40a42ae71a
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106230B2

Reaction notes

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