Acetic Acid → 2-Trimethylsilanylethyl (s)-4-(-2-tert-butoxycarbonylamino-2-carboxypent-4-enyl)piperidine-1-carboxylate

HRID 1743269Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@:9]([C:29]([O:31]C)=[O:30])([CH2:26][CH:27]=[CH2:28])[CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(NC(C(OC)=O)(CC=C)C[C@@H]1CCCCN1C(OCC[Si](C)(C)C)=O)=O)(C)(C)C.C[Si](C=[N+]=[N-])(C)C.C(O)(=O)C>CO.CCCCCC>[C:1]([O:5][C:6]([NH:8][C@@:9]([C:29]([OH:31])=[O:30])([CH2:26][CH:27]=[CH2:28])[CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([C:17]([O:19][CH2:20][CH2:21][Si:22]([CH3:23])([CH3:25])[CH3:24])=[O:18])[CH2:15][CH2:16]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Trimethylsilanylethyl (S)-4-(2-tert-butoxycarbonylamino-2-methoxycarbonylpent-4-enyl)piperidine-1-carboxylate 1.1 g of 2-trimethylsilanylethyl (S)-(2-tert-butoxycarbonylamino-2-methoxycarbonylpent-4-enyl)piperidine-1-carboxylate were dissolved in 33 ml of methanol and cooled to 0° C. 2.3 ml of a 2 N solution of trimethylsilyldiazomethane in hexane were added dropwise. The mixture was allowed to reach room temperature in the course of 3 h, and then a further 2.3 ml of the trimethylsilyldiazomethane solution were added dropwise. The mixture was stirred for 1 h and then the reaction was stopped by adding 1 ml of acetic acid. After stirring for 30 min, the solvents are removed in vacuo and the residue was chromatographed on silica gel.

Workup

customto reach room temperature in the course of 3 h
stirringAfter stirring for 30 min
customthe solvents are removed in vacuo
customthe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-bfe639ea030042e9978ad5ce7fd222ea
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07008957B2

Reaction notes

Loading…