Potassium Carbonate → 1-[2(S)-hydroxy-3(S)-amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-2-[tert-butoxycarbonyl]-hydrazine

HRID 1291788Notes

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, 2.0 g (4.10 mmol) of 1-[2(S)-hydroxy-3(S)-(trifluoroacetylamino)-4-phenyl-butyl]-1-[cyclohexylmethyl]-2-[tert-butoxycarbonyl]-hydrazine (Example 96b) dissolved in 316 ml of MeOH are heated to 70° C., 103 ml of 1M aqueous K2CO3 solution are added dropwise, and the mixture is stirred for 18 h at 70° C. The reaction mixture is concentrated by evaporation under HV 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: 1H-NMR (200 MHz, CD3OD): 1.42 (s, 9 H, Boc), 0.8-2.1 (m, 11H, cyclohexyl), 2.35-3.0 (m, 7H), 3.51 (m, 1H), 7.25 (m, 5H).

Workup

concentrationThe reaction mixture is concentrated by evaporation under HV
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-5ae2d8a1b4a74c3384a218f8e72f1dc7
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05753652

Reaction notes

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