Trimethylsilyl iodide → HCID 54197837, compound

HRID 1781310Notes

Reaction equation

C12CC(C=C1)CC2C1NC(C([O-])=O)CS1.C(OC([NH:23][CH2:24][C:25]([N:27]1[C@H:31]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][S:29][CH:28]1[CH:39]1[CH2:44][CH:43]2[CH2:45][CH:40]1[CH:41]=[CH:42]2)=[O:26])=O)(C)(C)C.I[Si](C)(C)C>>[NH2:23][CH2:24][C:25]([N:27]1[C@H:31]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][S:29][CH:28]1[CH:39]1[CH2:44][CH:43]2[CH2:45][CH:40]1[CH:41]=[CH:42]2)=[O:26]

Participants

Reactant 3

HCID 85247Trimethylsilyl iodide

HCID 19046189HCID 19046189, compound

HCID 54222219HCID 54222219, compound

Product 1

HCID 54197837HCID 54197837, compoundYield 99.8%

Procedure

tert-Butyl (4R)-3-2-aminoacetyl)-2-[(2RS)-5-norbornen-2-yl]-4-thiazolidinecarboxylate (mixture of isomers C and D) may be prepared in a manner similar to that described in Example 1B, but starting with 1.0 g of tert-butyl (4R)-3-(2-tert-butoxycarbonylaminoacetyl)-2-[(2RS)-5-norbornen-2-yl]-4-thiazolidinecarboxylate (mixture of isomers C and D) and 0.36 cm3 of iodotrimethylsilane. 0.77 g of tert-butyl (4R)-3-(2-aminoacetyl)-2-[(2RS)-5-norbornen-2-yl]-4-thiazolidinecarboxylate (mixture of isomers C and D) is thereby obtained in the form of a yellow oil, which is used in the subsequent syntheses without further treatment.

Sources & evidence

ORD record: ord-73543e7f76764526bdad67044d707af0
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05633270

Reaction notes

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