Acetic Acid → N-tert-Butoxycarbonyl-trans-4-(N,N-Dimethylglycylamino)-L-Proline

HRID 2185421Notes

Reaction equation

HRID 2185421 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:26])[C@@H:7]1[CH2:11][C@@H:10]([NH:12][C:13](=[O:18])[CH2:14][N:15]([CH3:17])[CH3:16])[CH2:9][N:8]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].CO.C(O)(=O)C>O.O1CCCC1>[C:22]([O:21][C:19]([N:8]1[CH2:9][C@H:10]([NH:12][C:13](=[O:18])[CH2:14][N:15]([CH3:16])[CH3:17])[CH2:11][C@H:7]1[C:6]([OH:26])=[O:5])=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 21341540N-tert-Butoxycarbonyl-trans-4-(N,N-Dimethylglycylamino)-L-Proline Methyl Ester

Product 1

HCID 21341539N-tert-Butoxycarbonyl-trans-4-(N,N-Dimethylglycylamino)-L-Proline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (40 mg) in water (1 mL) was added to a solution of N-tert-butoxycarbonyl-trans-4-(N,N-dimethylglycylamino)-L-proline methyl ester (A, 264 mg) in tetrahydrofuran (3 mL)-methanol (1 mL) at 0° C. After stirring at room temperature for 4 hr, acetic acid (55 L) was added to the reaction mixture at 0° C. The resulting solution was evaporated in vacuo to afford the crude title compound, which is used in the subsequent step.

Workup

  1. customThe resulting solution was evaporated in vacuo

Sources & evidence

ORD record
ord-543747a9b3074c3a9fc17da6471de2aa
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

Loading…