Triethylamine → (R)-2-[4-((S)-2-methoxycarbonyl-pyrrolidin-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 1864623Notes

Reaction equation

HRID 1864623 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[C:12]([O:14][CH3:15])=[O:13])[CH2:3][CH2:2]1.[O:16]=[C:17]1[N:23]([CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C@@H:33]([C:46](O)=[O:47])[CH2:34][C:35]3[CH:44]=[C:43]([CH3:45])[C:38]4[NH:39][C:40](=[O:42])[O:41][C:37]=4[CH:36]=3)=[O:31])[CH2:26][CH2:25]2)[CH2:22][CH2:21][C:20]2[CH:49]=[CH:50][CH:51]=[CH:52][C:19]=2[NH:18]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:16]=[C:17]1[N:23]([CH:24]2[CH2:25][CH2:26][N:27]([C:30]([O:32][C@H:33]([CH2:34][C:35]3[CH:44]=[C:43]([CH3:45])[C:38]4[NH:39][C:40](=[O:42])[O:41][C:37]=4[CH:36]=3)[C:46]([N:1]3[CH2:2][CH2:3][CH:4]([N:7]4[CH2:11][CH2:10][CH2:9][C@H:8]4[C:12]([O:14][CH3:15])=[O:13])[CH2:5][CH2:6]3)=[O:47])=[O:31])[CH2:28][CH2:29]2)[CH2:22][CH2:21][C:20]2[CH:49]=[CH:50][CH:51]=[CH:52][C:19]=2[NH:18]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 44607828(S)-Methyl 1-(piperidin-4-YL)pyrrolidine-2-carboxylateHCID 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 57973478(R)-2-[4-((S)-2-methoxycarbonyl-pyrrolidin-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

93 mg (0.44 mmol) methyl (S)-1-piperidin-4-yl-pyrrolidine-2-carboxylate were added to a solution of 200 mg (0.39 mmol) (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, 140 mg (0.44 mmol) TBTU and 61 μL (0.44 mmol) triethylamine in 2 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-27d123df24974a7f82b4ff92b3a8453b
Source dataset
uspto-grants-2009_12
Patent number
US07625886B2

Reaction notes

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