Triethylamine → (R)-2-[4-((S)-2-dimethylcarbamoylmethoxycarbonyl-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 1864625Notes

Reaction equation

HRID 1864625 reaction equation
O[CH2:2][C:3]([N:5]([CH3:7])[CH3:6])=[O:4].[O:8]=[C:9]1[N:15]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C@H:25]([CH2:42][C:43]3[CH:52]=[C:51]([CH3:53])[C:46]4[NH:47][C:48](=[O:50])[O:49][C:45]=4[CH:44]=3)[C:26]([N:28]3[CH2:33][CH2:32][CH:31]([N:34]4[CH2:38][CH2:37][CH2:36][C@H:35]4[C:39]([OH:41])=[O:40])[CH2:30][CH2:29]3)=[O:27])=[O:23])[CH2:18][CH2:17]2)[CH2:14][CH2:13][C:12]2[CH:54]=[CH:55][CH:56]=[CH:57][C:11]=2[NH:10]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:8]=[C:9]1[N:15]([CH:16]2[CH2:17][CH2:18][N:19]([C:22]([O:24][C@H:25]([CH2:42][C:43]3[CH:52]=[C:51]([CH3:53])[C:46]4[NH:47][C:48](=[O:50])[O:49][C:45]=4[CH:44]=3)[C:26]([N:28]3[CH2:29][CH2:30][CH:31]([N:34]4[CH2:38][CH2:37][CH2:36][C@H:35]4[C:39]([O:41][CH2:2][C:3](=[O:4])[N:5]([CH3:7])[CH3:6])=[O:40])[CH2:32][CH2:33]3)=[O:27])=[O:23])[CH2:20][CH2:21]2)[CH2:14][CH2:13][C:12]2[CH:54]=[CH:55][CH:56]=[CH:57][C:11]=2[NH:10]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 128746822-Hydroxy-N,N-dimethylacetamideHCID 16734820(R)-2-[4-((S)-2-carboxy-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

Product 1

HCID 57973446(R)-2-[4-((S)-2-dimethylcarbamoylmethoxycarbonyl-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

6 mg (0.06 mmol) 2-hydroxy-N,N-dimethyl-acetamide were added to a solution of 34 mg (0.05 mmol) (R)-2-[4-((S)-2-carboxy-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, 18 mg (0.06 mmol) TBTU and 8 μL 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 combined and lyophilised.

Workup

  1. customThe reaction solution was purified by HPLC
  2. additionthe fractions containing the product

Sources & evidence

ORD record
ord-e1de3203a81c44cebd06dc49039f93fe
Source dataset
uspto-grants-2009_12
Patent number
US07625886B2

Reaction notes

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