Isopropanol → H-Tyr(But)-O-CH(CH3)2 hydrochloride

HRID 904969Notes

Reaction equation

HRID 904969 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:15]([OH:17])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=1.[CH:28](O)([CH3:30])[CH3:29].CCCP(=O)=O.C(Cl)[Cl:39]>N1C=CC=CC=1>[NH2:1][C@H:2]([C:15]([O:17][CH:28]([CH3:30])[CH3:29])=[O:16])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[CH:8][CH:9]=1.[ClH:39]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6344DichloromethaneHCID 978520O-(1,1-Dimethylethyl)-N-((phenylmethoxy)carbonyl)-L-tyrosineHCID 16167369Propylphosphoric anhydride

Product 1

HCID 131713301H-Tyr(But)-O-CH(CH3)2 hydrochloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

18.6 g (50 mmoles) of Z-Tyr(But)-OH in 30 ml of pyridine are reacted with 30 ml of isopropanol and 40 ml of a 50 percent solution of propylphosphonic anhydride in methylene chloride analogously to Example 30 A. The resulting oil is subjected to catalytic hydrogenation analogously to Example 25 B. The substance crystallizes from ether. Yield 13.15 g (83%), melting point 161°-163°, [α]D23 =+15.7° (c=1, methanol).

Workup

  1. customThe substance crystallizes from ether
  2. customYield 13.15 g (83%), melting point 161°-163°, [α]D23 =+15.7° (c=1, methanol)

Sources & evidence

ORD record
ord-de349d54dcca41ce95aa76394d9acfb9
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

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