Methanol → (S)-tert-butyl 3-amino-4-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-4-oxobutanoate

HRID 718929Notes

Reaction equation

HRID 718929 reaction equation
C1C2C(COC([NH:18][C@H:19]([C:28]([N:30]([CH2:40][C:41]3[C:42]4[CH:49]=[CH:48][CH:47]=[CH:46][C:43]=4[S:44][CH:45]=3)[C@@H:31]([CH3:39])[CH:32]([O:36][CH2:37][CH3:38])[O:33][CH2:34][CH3:35])=[O:29])[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1.CC(=O)OCC.CO>C(Cl)Cl>[NH2:18][C@H:19]([C:28]([N:30]([CH2:40][C:41]1[C:42]2[CH:49]=[CH:48][CH:47]=[CH:46][C:43]=2[S:44][CH:45]=1)[C@@H:31]([CH3:39])[CH:32]([O:36][CH2:37][CH3:38])[O:33][CH2:34][CH3:35])=[O:29])[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 8082PiperidineHCID 8857Ethyl AcetateHCID 67075020(S)-tert-Butyl 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-4-oxobutanoate

Product 1

HCID 67075220(S)-tert-butyl 3-amino-4-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-4-oxobutanoateYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

(S)-tert-Butyl 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-4-oxobutanoate (Compound III-18) 18.5 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 10.2 g, (yield 81%).

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-109f734e2eed46c6b8cb837fc9c553a7
Source dataset
uspto-grants-2015_11
Patent number
US09193734B2

Reaction notes

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