Triethylamine → (r)-2-[4-(4-Ethoxycarbonylmethyl-piperazin-1-yl)-piperidin-1-yl]-1-(4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-ylmethyl)-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

HRID 1864622Notes

Reaction equation

HRID 1864622 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9][CH2:8]2)[CH2:3][CH2:2]1.[O:19]=[C:20]1[N:26]([CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C@@H:36]([C:49](O)=[O:50])[CH2:37][C:38]3[CH:47]=[C:46]([CH3:48])[C:41]4[NH:42][C:43](=[O:45])[O:44][C:40]=4[CH:39]=3)=[O:34])[CH2:29][CH2:28]2)[CH2:25][CH2:24][C:23]2[CH:52]=[CH:53][CH:54]=[CH:55][C:22]=2[NH:21]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[O:19]=[C:20]1[N:26]([CH:27]2[CH2:28][CH2:29][N:30]([C:33]([O:35][C@H:36]([CH2:37][C:38]3[CH:47]=[C:46]([CH3:48])[C:41]4[NH:42][C:43](=[O:45])[O:44][C:40]=4[CH:39]=3)[C:49]([N:1]3[CH2:6][CH2:5][CH:4]([N:7]4[CH2:12][CH2:11][N:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9][CH2:8]4)[CH2:3][CH2:2]3)=[O:50])=[O:34])[CH2:31][CH2:32]2)[CH2:25][CH2:24][C:23]2[CH:52]=[CH:53][CH:54]=[CH:55][C:22]=2[NH:21]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57848475Ethyl(4-piperidin-4-yl-piperazin-1-yl)-acetateHCID 68608307(R)-1-carboxy-2-(4-methyl-2-oxo-2,3-dihydrobenzoxazol-6-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Product 1

HCID 16734421(r)-2-[4-(4-Ethoxycarbonylmethyl-piperazin-1-yl)-piperidin-1-yl]-1-(4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-ylmethyl)-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

56 mg (0.22 mmol) ethyl (4-piperidin-4-yl-piperazin-1-yl)-acetate were added to a solution of 100 mg (0.20 mmol) (R)-1-carboxy-2-(4-methyl-2-oxo-2,3-dihydrobenz-oxazol-6-yl)-ethyl 4-(2-oxo-1,2,4,5,-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate, 71 mg (0.22 mmol) TBTU and 31 μL (0.22 mmol) triethylamine in 1 mL DMF and the reaction mixture was shaken overnight at RT. The reaction solution was purified by HPLC without working up; the fractions containing the product were concentrated by evaporation and lyophilised.

Workup

  1. customThe reaction solution was purified by HPLC
  2. additionthe fractions containing the product
  3. concentrationwere concentrated by evaporation

Sources & evidence

ORD record
ord-60bda734e8e54a0ba9de507a3162551d
Source dataset
uspto-grants-2009_12
Patent number
US07625886B2

Reaction notes

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