Water → HCID 68437290, compound

HRID 276714Notes

Reaction equation

FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:14]([O:21][C:22](=[O:45])[NH:23][CH:24]([C:29](=[O:44])[NH:30][CH:31]([C:41](=O)[NH2:42])[CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:25][CH:26]([CH3:28])[CH3:27])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.O>O1CCCC1>[CH2:14]([O:21][C:22](=[O:45])[NH:23][CH:24]([C:29](=[O:44])[NH:30][CH:31]([C:41]#[N:42])[CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:25][CH:26]([CH3:27])[CH3:28])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: -5 °C

Procedure

0.3 ml of trifluoroacetic acid anhydride is added dropwise to a solution of 0.9 g of [1-(2-benzyloxy-1-carbamoyl-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester and 0.6 ml of triethylamine in 15 ml of tetrahydrofuran at −5° C. The reaction mixture is stirred at −5° C. for 3 hours and then for 12 hours at room temperature. The reaction mixture is then poured into H2O and the aqueous layer is extracted three times with ethyl acetate. The combined organic layers are washed once with H2O and once with brine, then dried over sodium sulfate, the solvent is removed and the residue is crystallized from diethylether/hexane. Mp.: 126-127° C.

Workup

waitfor 12 hours at room temperature
extractionthe aqueous layer is extracted three times with ethyl acetate
washThe combined organic layers are washed once with H2O and once with brine
dry with materialdried over sodium sulfate
customthe solvent is removed
customthe residue is crystallized from diethylether/hexane

Sources & evidence

ORD record: ord-f3663c2cf9a14ac7a136fceac8858ede
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353017B1

Reaction notes

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