Potassium Carbonate → HCID 10763050, compound

HRID 1291781Notes

Reaction equation

[OH:1][C@@H:2]([C@@H:20]([NH:28]C(=O)C(F)(F)F)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][N:4]([CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C([O-])([O-])=O.[K+].[K+]>CO>[OH:1][C@@H:2]([C@@H:20]([NH2:28])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][N:4]([CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

Conditions

Temperature: 70 °C

Procedure

Under a nitrogen atmosphere, 326 mg (0.669 mmol) of 1-[2(R)-hydroxy-3(S)-(trifluoroacetylamino)-4-phenyl-butyl]-1-[cyclohexylmethyl]-2-[tert-butoxycarbonyl]-hydrazine dissolved in 52 ml of MeOH are heated to 70° C., 17 ml of 1M aqueous K2CO3 solution are added dropwise and the mixture is stirred for 16 h at 70° C. The reaction mixture is concentrated by evaporation and the residue is partitioned between 3 portions of methylene chloride, 2 portions of water and brine. Concentration by evaporation of the organic phases which have been dried with Na2SO4 yields the title compound, which is used directly in the next step: 1H-NMR (200 MHz, CD3OD): 1.42 (s, 9 H, Boc), 0.8-2.1 (m, 11 H, cyclohexyl), 2.4-3.0 (m, 6H), 3.1 (m, 1H), 3.54 (m, 1H), 7.28 (m, 5H).

Workup

concentrationThe reaction mixture is concentrated by evaporation
customthe residue is partitioned between 3 portions of methylene chloride, 2 portions of water and brine
concentrationConcentration
customby evaporation of the organic phases which
dry with materialhave been dried with Na2SO4

Sources & evidence

ORD record: ord-35cd5f2b64584ad1b7cc0fd40001e8e5
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05753652

Reaction notes

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