Methanol → HCID 86698544, compound

HRID 718926Notes

Reaction equation

HRID 718926 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:36]CC1C2C=CC=CC=2C2C1=CC=CC=2)[C:14]([N:16]([C@@H:27]([CH3:35])[CH:28]([O:32][CH2:33][CH3:34])[O:29][CH2:30][CH3:31])[CH2:17][C:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[S:20][CH:19]=1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCCCC1.CC(=O)OCC.CO>C(Cl)Cl>[NH2:36][C@H:13]([C:14]([N:16]([CH2:17][C:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[S:20][CH:19]=1)[C@@H:27]([CH3:35])[CH:28]([O:29][CH2:30][CH3:31])[O:32][CH2:33][CH3:34])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8082PiperidineHCID 8857Ethyl AcetateHCID 67088457HCID 67088457, compound2×

Product 1

HCID 86698544HCID 86698544, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

6-tert-butoxycarbonylamino-2-(S)-(9H-fluoren-9-yl)methylamino-N—((S)-1,1-diethoxypropan-2-yl)-N-(benzothiophen-3-ylmethyl)hexanamide (Compound III-15) 20.1 g (27 mmol) and piperidine 22.7 g (270 mmol) were added in DCM (90 ml). The mixture was stirred for 1.5 h at room temperature. The mixture was diluted with DCM (200 ml) and washed with water (150 ml×3). The solution was concentrated in vacuo. The residue was purified by column chromatography on silica gel with PE:EA=50:1 to DCM:MeOH=10:1 to give the title compound 11.7 g, (yield 83%).

Workup

  1. washwashed with water (150 ml×3)
  2. concentrationThe solution was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel with PE

Sources & evidence

ORD record
ord-d209635b16114981a34c1d81a6337b4d
Source dataset
uspto-grants-2015_11
Patent number
US09193734B2

Reaction notes

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