2-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid → 3-Hydroxy-1-adamantyl-D-glycine

HRID 17765Notes

Reaction equation

HRID 17765 reaction equation
CC(C)(OC([NH:7][C@@H:8]([C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][C:14]([OH:22])([CH2:15]3)[CH2:13]1)[CH2:19]2)[C:9]([OH:11])=[O:10])=O)C.OC12CC3CC(CC(C(=O)C(O)=O)(C3)C1)C2>>[NH2:7][C@@H:8]([C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][C:14]([OH:22])([CH2:15]3)[CH2:13]1)[CH2:19]2)[C:9]([OH:11])=[O:10]

Participants

3

Reactant 2

HCID 104661932-(3-Hydroxy-1-adamantyl)-2-oxoacetic acidHCID 11723843(2S)-((tert-Butoxycarbonyl)amino)(3-hydroxytricyclo(3.3.1.1 3,7)dec-1-yl)acetic acid

Product 1

HCID 102630783-Hydroxy-1-adamantyl-D-glycine

Procedure

U.S. application Ser. No. 10/716,012 filed Nov. 18, 2003 discloses a method for preparing (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid which utilizes 3-hydroxy-α-oxotricyclo[3.3.1.13,7]-decane-1-acetic acid as a starting material and wherein an enzymatic reductive amination is used to prepare and isolate (αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid which is converted to the desired product in a separate step.

Workup

  1. customto prepare

Sources & evidence

ORD record
ord-93f05cba044e4d04b53b4d2ebed98895
Source dataset
uspto-grants-2010_06
Patent number
US07741082B2

Reaction notes

Loading…