HCID 71227390, compound → HCID 86690221, compound

HRID 2370003Notes

Reaction equation

HRID 2370003 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([O:15][C:16]([NH:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]1[NH:25][C@H:26]1[CH2:30][CH2:29][N:28]([C:31]2[CH:41]=[CH:40][C:34]([C:35]([O:37][CH2:38]C)=[O:36])=[CH:33][CH:32]=2)[CH2:27]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O.CO>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([O:15][C:16]([NH:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]1[NH:25][C@H:26]1[CH2:30][CH2:29][N:28]([C:31]2[CH:41]=[CH:40][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=2)[CH2:27]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 71227390HCID 71227390, compound

Product 1

HCID 86690221HCID 86690221, compoundYield 26.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a round bottom flask was added ethyl 4-((S)-3-((1R,2R)-2-(benzyloxycarbonylamino)cyclohexylamino)pyrrolidin-1-yl)benzoate trifluoroacetate (30 mg, 0.052 mmol), LiOH monohydrate (37 mg, 1.56 mmol) in water (1 ml) and MeOH (1 ml). The reaction was stirred at rt for 16 hrs. The reaction was concentrated and the residue was purified by RP prep-HPLC to afford methyl 4-((S)-3-((1R,2R)-2-(benzyloxycarbonylamino)cyclohexylamino)pyrrolidin-1-yl)benzoate trifluoroacetate (8 mg, 0.014 mmol, 26.8% yield) as a beige solid. Anal. Calcd. for C26H33N3O4 m/z 451.5, found: 452.3 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.90 (d, J=8.8 Hz, 2H), 7.45-7.31 (m, 1H), 7.29-7.15 (m, 4H), 6.67 (d, J=8.8 Hz, 2H), 4.93 (s, 2H), 4.63 (d, J=12.2 Hz, 1H), 4.25-4.11 (m, 1H), 3.72-3.39 (m, 4H), 3.23-3.12 (m, 1H), 2.61-2.42 (m, 1H), 2.40-2.19 (m, 2H), 2.09-1.95 (m, 1H), 1.94-1.77 (m, 2H), 1.63-1.23 (m, 4H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by RP prep-HPLC

Sources & evidence

ORD record
ord-697f8f40463441ca967a758eff798d36
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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