HCID 131721327, compound → HCID 131721329, compound

HRID 1584252Notes

Reaction equation

HRID 1584252 reaction equation
CC(OC([NH:8][C@@H:9]([C:23]([OH:25])=[O:24])[CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)(C)C.[NH:26]1[CH2:33][CH2:32][CH2:31][C@H:27]1[C:28]([OH:30])=[O:29]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH:14]1[CH:13]=[CH:12][C:11]([CH:10]([C@@H:9]([NH2:8])[C:23]([OH:25])=[O:24])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:16][CH:15]=1.[NH:26]1[CH2:33][CH2:32][CH2:31][C@H:27]1[C:28]([OH:30])=[O:29]

Participants

3

Reactant 1

HCID 131721327HCID 131721327, compound

Product 1

HCID 131721329HCID 131721329, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of Boc-D-3,3-diphenylalanine-L-proline-N-(trans-4-imidazoleallyl) amide (55 mg, 0.1 mmol) in 2:1 methylene chloride/TFA (30 ml) was stirred at room temperature for 4 h. The solvents were removed in vacuo and the residue was purified by preparative HPLC. 1H NMR (CH3OD) d 1.10-1.37 (m, 2 H), 1.70-1.90 (br s, 2 H), 2.70-2.90 (br m, 1 H), 3.50-3.65 (br m, 1 H) 3.95 (br s, 2 H), 4.00-4.10 (br m, 1 H), 4.45 (d, J=11.5 Hz, 1 H), 4.95 (d, J=11.5 Hz, 1 H) 6.30-6.40 (m, 1 H), 6.58 (d, J=16 Hz, 1 H), 7.25-7.70 (m, 11 H), 7.85 (s, 1 H); MS (FAB) 444 (M+1)+.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3a3eadbf0a5242aabf8e620b30967716
Source dataset
uspto-grants-1999_08
Patent number
US05932606

Reaction notes

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