Dichloromethane → [(1R)-2-AMINO-1-PHENYLETHYL]-CARBAMIC ACID 1,1-DIMETHYLETHYL ESTER

HRID 1826601Notes

Reaction equation

HRID 1826601 reaction equation
[C:1]([NH:8][C@H:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:10][N:11]=[N+]=[N-])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Cl)Cl.CCOC(C)=O.C(N(CC)CC)C>CO.C1COCC1>[C:1]([NH:8][C@H:9]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:10][NH2:11])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 20790081HCID 20790081, compound

Product 1

HCID 15675183[(1R)-2-AMINO-1-PHENYLETHYL]-CARBAMIC ACID 1,1-DIMETHYLETHYL ESTERYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using a similar hydrogenolysis procedure to that described as Deprotection Method A, (R)-2-(Boc-amino)-2-phenylethylazide (32.5 g, 124 mmol) in methanol (200 mL) and THF (300 mL) afforded, after chromatography (SiO2, 10:5:1 CH2Cl2, EtOAc, triethylamine), 24.0 g (82%) of the title compound.

Workup

  1. customafforded

Sources & evidence

ORD record
ord-636a1ae12c54437e8b2f33d02baaea63
Source dataset
uspto-grants-2006_05
Patent number
US07053078B2

Reaction notes

Loading…