Trifluoroacetic acid → H-D-Phe-Ala-OH

HRID 223104Notes

Reaction equation

C([O:5][C:6]([C@@H:8]([N:10]1[C@@H:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:12]([N:20]=[N+]=[N-])[C:11]1=[O:23])[CH3:9])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>>[NH2:20][C@@H:12]([C:11]([NH:10][C@H:8]([C:6]([OH:7])=[O:5])[CH3:9])=[O:23])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 130352151-(1(S)-t-butoxycarbonylethyl)-3(R)-azido-4(S)-phenylazetidin-2-one

Product 1

HCID 6993122H-D-Phe-Ala-OHYield 140.8%

Procedure

According to the same procedure as in Example 15 except that 1-(1(S)-t-butoxycarbonylethyl)-3(R)-azido-4(S)-phenylazetidin-2-one (300 mg., 0.95 mmol) was used as a starting material, trifluoroacetic acid salt of D-phenylalanyl-L-alanine (316 mg., yield: 95%) was obtained.

Sources & evidence

ORD record: ord-6ba22c4ffe3d4cb188eceb4e96ce8e4a
Source dataset: uspto-grants-1982_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04352752

Reaction notes

Loading…