Trifluoroacetic acid → H-D-Tyr(Me)-L-Ile-D-Pro-OBzl-TFA

HRID 1725104Notes

Reaction equation

HRID 1725104 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:12]([NH:14][C@H:15]([C:20]([N:22]1[CH2:36][CH2:35][CH2:34][C@@H:23]1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=[O:21])[C@H:16]([CH2:18][CH3:19])[CH3:17])=[O:13])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]>>[NH2:1][C@@H:2]([C:12]([NH:14][C@H:15]([C:20]([N:22]1[CH2:36][CH2:35][CH2:34][C@@H:23]1[C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])=[O:21])[C@H:16]([CH2:18][CH3:19])[CH3:17])=[O:13])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.[F:47][C:46]([C:44]([OH:50])=[O:45])([F:49])[F:48]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 58726683Boc-D-Tyr(Me)-L-Ile-D-Pro-OBzl

Product 1

HCID 131727276H-D-Tyr(Me)-L-Ile-D-Pro-OBzl-TFA

Procedure

Boc-D-Tyr(Me)-L-Ile-D-Pro-OBzl (1.19 g, 2.0 mmol) was dissolved in TFA (5 ml) and left with standing on ice for 30 minutes. On completion of the reaction, TFA was removed by evaporation, and the residue was vacuum-dried to obtain H-D-Tyr(Me)-L-Ile-D-Pro-OBzl.TFA. The compound was dissolved in DMF (4.0 ml), and Boc-L-Ab8-OH (676 mg, 2.0 mmol) was then added. HBTU (1.14 g, 3.0 mmol), HOBt.H2O (306 mg, 2.0 mmol), and triethylamine (1.4 ml, 10 mmol) were further added and stirred for 3 hours under ice-cooling. The reaction solution was concentrated, dissolved in ethyl acetate, and successively washed with an aqueous 10% citric acid solution, an aqueous 4% sodium bicarbonate solution, and saturated saline. The product was dried over MgSO4 and concentrated, and the resulting foam substance was purified by flash silica gel chromatography (4×30 cm, 2% methanol/chloroform) to obtain the foam title compound (1.44 g, 1.76 mmol, 88% yield). HPLC retention time: 10.9 min.

Workup

  1. waitleft
  2. customwas removed by evaporation
  3. customthe residue was vacuum-dried

Sources & evidence

ORD record
ord-6c8450c260c5448cb00f673830f0c7bb
Source dataset
uspto-grants-2009_02
Patent number
US07488712B2

Reaction notes

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