N-Boc-dehydroalanine ethyl ester → 2-(N-Boc)amino-3-[4-(2-methyl-10H-thieno[2,3-b][1,5]benzodiazepin-4-yl)-piperazin-1-yl]-propionic acid, ethyl ester

HRID 72309Notes

Reaction equation

HRID 72309 reaction equation
[CH3:1][C:2]1[S:21][C:5]2[NH:6][C:7]3[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=3[N:9]=[C:10]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:4]=2[CH:3]=1.[CH2:22]([O:24][C:25](=[O:36])[C:26](=[CH2:35])[NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH3:23]>CCO>[C:28]([NH:27][CH:26]([CH2:35][N:14]1[CH2:15][CH2:16][N:11]([C:10]2[C:4]3[CH:3]=[C:2]([CH3:1])[S:21][C:5]=3[NH:6][C:7]3[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=3[N:9]=2)[CH2:12][CH2:13]1)[C:25]([O:24][CH2:22][CH3:23])=[O:36])([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29]

Participants

4

Reactant 2

HCID 13467840N-Boc-dehydroalanine ethyl esterHCID 135446209Desmethylolanzapine2×

Product 1

HCID 1360372732-(N-Boc)amino-3-[4-(2-methyl-10H-thieno[2,3-b][1,5]benzodiazepin-4-yl)-piperazin-1-yl]-propionic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-methyl-4-(1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine, compound D above, (0.14 g, 0.46 mmol, 1 eq) and N-Boc-dehydroalanine ethyl ester (G, 0.1 g, 0.46 mmol, 1 eq) in 4 ml of anhydrous EtOH was refluxed at 60-65° C. overnight. The solvent was evaporated to dryness and the crude product was purified by flash chromatography (eluent—40% EtOAc in Hexanes). Yield—0.15 g (65%)

Workup

  1. customThe solvent was evaporated to dryness
  2. customthe crude product was purified by flash chromatography (eluent—40% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-db0c41d19a864fbdb2d50f869e7b9b1a
Source dataset
uspto-grants-2014_09
Patent number
US08828993B2

Reaction notes

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