Trifluoroacetic acid → HCID 178427526, compound

HRID 247515Notes

Reaction equation

[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:2]([C:7]([OH:9])=O)[CH2:3][CH:4]([CH3:6])[CH3:5].O.CN1CCOCC1.C(Cl)(=O)OCC.C(O)(C(F)(F)F)=O.[NH2:38][C@H:39]([C:57]([NH2:59])=[O:58])[CH2:40][CH2:41][CH2:42][NH:43][C:44](=[NH:56])[NH:45][S:46]([C:49]1[CH:55]=[CH:54][C:52]([CH3:53])=[CH:51][CH:50]=1)(=[O:48])=[O:47]>CN(C)C=O>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:2]([C:7]([NH:38][C@H:39]([C:57]([NH2:59])=[O:58])[CH2:40][CH2:41][CH2:42][NH:43][C:44](=[NH:56])[NH:45][S:46]([C:49]1[CH:55]=[CH:54][C:52]([CH3:53])=[CH:51][CH:50]=1)(=[O:48])=[O:47])=[O:9])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

Conditions

Temperature: -20 °C

Procedure

2.493 g of Boc-D-Leu-OH.H2O was dissolved in 10 ml of dimethylformamide. The solution was cooled to -20° C. 1.1 ml of N-methylmorpholine and 0.96 ml of ethyl chlorocarbonate were added to the solution. After 5 min, a solution of 4.414 g of CF3COOH.H-Arg(Tos)-NH2 and 1.65 ml of N-methylmorpholine in 20 ml of dimethylformamide was added thereto and the mixture was stirred at about -5° C. for 2 h. After concentration, the residue was dissolved in ethyl acetate and washed with NaHCO3 and water successively. After concentration, ether was added thereto to solidify the product. Thus, 4.96 g of Boc-D-Leu-Arg(Tos)-NH2 was obtained.

Workup

concentrationAfter concentration
dissolutionthe residue was dissolved in ethyl acetate
washwashed with NaHCO3 and water successively
concentrationAfter concentration, ether
additionwas added

Sources & evidence

ORD record: ord-6ad2ba2a38aa4476a4a8fdce6e0a6f16
Source dataset: uspto-grants-1987_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04707468

Reaction notes

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