tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate → (1,1-dimethyl ethyl) O-(4-ethoxy-4-oxobutyl)-N-[1-(phenylmethyl)-1H-tetrazol-5-yl]-L-tyrosinate

HRID 1759701Notes

Reaction equation

HRID 1759701 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:24]=[CH:23][C:12]([CH2:13][C@@H:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[NH2:15])=[CH:11][CH:10]=1)[CH3:2].F[C:27]1[N:31]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:30]=[N:29][N:28]=1>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C@@H:14]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[NH:15][C:27]2[N:31]([CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:30]=[N:29][N:28]=2)=[CH:23][CH:24]=1)[CH3:2]

Participants

4

Reactant 2

HCID 15512208tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionateHCID 219422015-Fluoro-1-(phenylmethyl)-1h-tetrazole

Product 1

HCID 69733478(1,1-dimethyl ethyl) O-(4-ethoxy-4-oxobutyl)-N-[1-(phenylmethyl)-1H-tetrazol-5-yl]-L-tyrosinateYield 57.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of aminoester 4-2 (325 mg, 0.92 mmole) and 5-fluoro-1-(phenylmethyl)-1H-tetrazole (170 mg, 0.95 mmole) in 15 ml of pyridine is heated at 100° C. for 2 hours. Evaporation is then carried out under reduced pressure until a dry extract is obtained which is purified by chromatography eluting with a heptane/AcOEt mixture 50/50. 270 mg of the expected product 5-1 is obtained.

Workup

  1. customEvaporation
  2. extractionextract
  3. customis obtained which
  4. customis purified by chromatography
  5. washeluting with a heptane/AcOEt mixture 50/50

Sources & evidence

ORD record
ord-096b386501d94393b4aa670defd2ed61
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

Loading…