Trimethylsilyl iodide → HCID 11044929, compound

HRID 976008Notes

Reaction equation

HRID 976008 reaction equation
C(OC([NH:8][CH2:9][C:10]([N:12]1[C@@H:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][CH2:21][C@H:13]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:11])=O)(C)(C)C.I[Si](C)(C)C>C(Cl)(Cl)Cl>[NH2:8][CH2:9][C:10]([N:12]1[C@@H:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:22][CH2:21][C@H:13]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:11]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 57302214HCID 57302214, compound

Product 1

HCID 11044929HCID 11044929, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

tert-Butyl (2S,5R)-1-(2-aminoacetyl)-5-phenylprolinate may be obtained in a fashion similar to that described in Example 2 A, but starting from 1.22 g of tert-butyl (2S,5R)-1-(2-tert-butoxycarbonylaminoacetyl)-5-phenylprolinate, 0.45 cm3 of iodotrimethylsilane in solution in 30 cm3 of anhydrous chloroform. 0.79 g of tert-butyl (2S,5R)-1-(2-aminoacetyl)-5-phenylprolinate is thus obtained in the form of an oil, used as it is in subsequent syntheses.

Sources & evidence

ORD record
ord-0f2f01782d8c4f64a51cf3320efe2692
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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