Dimethylformamide → HCID 14503271, compound

HRID 366940Notes

Reaction equation

[C:1]([NH:8][C@H:9]([C:11]([NH:13][C@H:14]([C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=O)=[O:17])[CH3:15])=[O:12])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN1CCOCC1.Cl.[NH2:34][CH:35]([CH:42]([CH3:44])[CH3:43])[CH:36]([OH:41])[C:37]([F:40])([F:39])[F:38].CN(C)C=O>C(#N)C.C(OC(Cl)=O)C(C)C>[F:38][C:37]([F:39])([F:40])[CH:36]([OH:41])[CH:35]([NH:34][C:20](=[O:22])[C@@H:19]1[CH2:23][CH2:24][CH2:25][N:18]1[C:16](=[O:17])[C@H:14]([CH3:15])[NH:13][C:11](=[O:12])[C@H:9]([CH3:10])[NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])[CH:42]([CH3:43])[CH3:44]

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of Boc-L-alanyl-L-alanyl-L-proline (1.0 g, 2.80 mmol) in dry acetonitrile (25 ml) was added N-methylmorpholine (0.34 ml, 3.06 mmol). The solution was cooled to -20° C. and isobutylchloroformate (0.37 ml, 2.88 nmol) was added dropwise. To this solution, a pre-cooled (-20° C.) mixture of 3-amino-1,1,1-trifluoro-4-methyl-2-pentanol hydrochloride (0.61 g, 2.91 mmol), N,N-dimethylformamide (4 ml) and N-methylmorpholine (0.34, 3.06 mmol) was added. The reaction mixture was stirred at -20° C. for 4 hr, allowed to warm to room temperature and stirred overnight. Removal of the solvents in vacuo produced a pale yellow residue, which was purified by flash chromatography using ethyl acetate as an eluent to give 1,1,1-Trifluoro-3-[(N-tert-butyloxycarbonylalanyl) alanyl-prolylamino]-4-methylpentane-2-ol (1.09 g, 2.1 mmol) in 76% yield.

Workup

temperatureTo this solution, a pre-cooled
additionwas added
temperatureto warm to room temperature
stirringstirred overnight
customRemoval of the solvents in vacuo
customproduced a pale yellow residue, which
customwas purified by flash chromatography

Sources & evidence

ORD record: ord-e6dd2983c2d945eabed0987bb898fe98
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130315

Reaction notes

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