Methanol → (S)-2-amino-N1-(benzo[b]thiophen-3-ylmethyl)-N1-((S)-1,1-diethoxy-propan-2-yl)-N4-tritylsuccinamide

HRID 718932Notes

Reaction equation

HRID 718932 reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][N:7]([C@@H:52]([CH3:60])[CH:53]([O:57][CH2:58][CH3:59])[O:54][CH2:55][CH3:56])[C:8](=[O:51])[C@@H:9]([NH:33]C(=O)OCC2C3C=CC=CC=3C3C2=CC=CC=3)[CH2:10][C:11](=[O:32])[NH:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]2[CH:61]=[CH:62][CH:63]=[CH:64][C:2]1=2.N1CCCCC1.CC(=O)OCC.CO>C(Cl)Cl>[NH2:33][C@@H:9]([CH2:10][C:11]([NH:12][C:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:32])[C:8]([N:7]([CH2:6][C:4]1[C:3]2[CH:61]=[CH:62][CH:63]=[CH:64][C:2]=2[S:1][CH:5]=1)[C@@H:52]([CH3:60])[CH:53]([O:54][CH2:55][CH3:56])[O:57][CH2:58][CH3:59])=[O:51]

Participants

6

Reactant 4

HCID 887MethanolHCID 8082PiperidineHCID 8857Ethyl AcetateHCID 131730614(9H-Fluoren-9-yl)methyl(S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-1,4-dioxo-4-(tritylamino)butan-2-ylcarbamate

Product 1

HCID 67075021(S)-2-amino-N1-(benzo[b]thiophen-3-ylmethyl)-N1-((S)-1,1-diethoxy-propan-2-yl)-N4-tritylsuccinamideYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

(9H-Fluoren-9-yl)methyl (S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-1,4-dioxo-4-(tritylamino)butan-2-ylcarbamate (Compound III-21) 23.5 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 15.1 g, (yield 86%).

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-7a111c72829d456cbd8a0da7d7e71311
Source dataset
uspto-grants-2015_11
Patent number
US09193734B2

Reaction notes

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