(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid → HCID 54422886, compound

HRID 2260389Notes

Reaction equation

C(OC(N1[C@@H](C2C=CC=CC=2)[C@H](C(O)=O)OC1(C)C)=O)(C)(C)C.[C:24]([O:28][C:29]([N:31]1[C@@H:35]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@H:34]([C:42]([O:44]CC)=[O:43])[O:33][C:32]1([CH2:49][CH3:50])[CH2:47][CH3:48])=[O:30])([CH3:27])([CH3:26])[CH3:25]>>[C:24]([O:28][C:29]([N:31]1[C@@H:35]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C@H:34]([C:42]([OH:44])=[O:43])[O:33][C:32]1([CH2:49][CH3:50])[CH2:47][CH3:48])=[O:30])([CH3:27])([CH3:26])[CH3:25]

Participants

Reactant 2

HCID 10969286(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid

HCID 54436966HCID 54436966, compound

Product 1

HCID 54422886HCID 54422886, compoundYield 79.8%

Procedure

(4S,5R)-3-tert-Butoxycarbonyl-2,2-diethyl-4-phenyl-5-oxazolidinecarboxylic acid may be obtained under the conditions described in Example 6 for the preparation of (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid. Thus, starting with 2.3 g of ethyl (4S,5R)-3-tert-butoxycarbonyl-2,2-diethyl-4-phenyl-5-oxazolidinecarboxylate, 1.7 g of (4S,5R)-3-tert-butoxycarbonyl-2,2-diethyl-4-phenyl-5-oxazolidinecarboxylic acid is obtained in the form of white crystals, melting point 185° C.

Sources & evidence

ORD record: ord-45d52ba0e02a4a159994600b5513d0eb
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05476954

Reaction notes

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