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

HRID 1743269
Notes
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Reaction equation

HRID 1743269 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 167693Trimethylsilyldiazomethane2×HCID 909187592-Trimethylsilanylethyl (s)-4-(2-tert-butoxycarbonylamino-2-methoxycarbonylpent-4-enyl)piperidine-1-carboxylateHCID 1317253752-Trimethylsilanylethyl (s)-(2-tert-butoxycarbonylamino-2-methoxycarbonylpent-4-enyl)piperidine-1-carboxylate

Product 1

HCID 90861707
2-Trimethylsilanylethyl (s)-4-(-2-tert-butoxycarbonylamino-2-carboxypent-4-enyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

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

  1. customto reach room temperature in the course of 3 h
  2. stirringAfter stirring for 30 min
  3. customthe solvents are removed in vacuo
  4. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes