Triethylamine → Dimethylcarbamoylmethyl 1'-{(r)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]propionyl}-1,4'-bipiperidinyl-4-carboxylate

HRID 730681Notes

Reaction equation

HRID 730681 reaction equation
O[CH2:2][C:3]([N:5]([CH3:7])[CH3:6])=[O:4].[CH2:8]([O:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH2:23][C@@H:24]([O:42][C:43]([N:45]2[CH2:50][CH2:49][CH:48]([N:51]3[CH2:57][CH2:56][C:55]4[CH:58]=[CH:59][CH:60]=[CH:61][C:54]=4[NH:53][C:52]3=[O:62])[CH2:47][CH2:46]2)=[O:44])[C:25]([N:27]2[CH2:32][CH2:31][CH:30]([N:33]3[CH2:38][CH2:37][CH:36]([C:39]([OH:41])=[O:40])[CH2:35][CH2:34]3)[CH2:29][CH2:28]2)=[O:26])=[CH:18][C:17]=1[CH3:63])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:8]([O:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH2:23][C@@H:24]([O:42][C:43]([N:45]2[CH2:46][CH2:47][CH:48]([N:51]3[CH2:57][CH2:56][C:55]4[CH:58]=[CH:59][CH:60]=[CH:61][C:54]=4[NH:53][C:52]3=[O:62])[CH2:49][CH2:50]2)=[O:44])[C:25]([N:27]2[CH2:32][CH2:31][CH:30]([N:33]3[CH2:34][CH2:35][CH:36]([C:39]([O:41][CH2:2][C:3](=[O:4])[N:5]([CH3:7])[CH3:6])=[O:40])[CH2:37][CH2:38]3)[CH2:29][CH2:28]2)=[O:26])=[CH:18][C:17]=1[CH3:63])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 128746822-Hydroxy-N,N-dimethylacetamideHCID 672736911'-{(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl}-1,4'-bipiperidinyl-4-carboxylic acid

Product 1

HCID 67273082Dimethylcarbamoylmethyl 1'-{(r)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]propionyl}-1,4'-bipiperidinyl-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

30 mg (0.29 mmol) 2-hydroxy-N,N-dimethyl-acetamide were added at RT to a solution of 200 mg (0.25 mmol) 1′-{(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl}-1,4′-bipiperidinyl-4-carboxylic acid (Example 6.1a), 90 mg (0.28 mmol) TBTU and 80 μL (3.73 mmol) triethylamine in 1.8 mL DMF and this was stirred for 20 h at RT. The reaction mixture was poured onto saturated NaHCO3 solution, the precipitate formed was suction filtered and dried. Further purification was carried out by HPLC, the fractions containing the product were combined and lyophilised.

Workup

  1. customthe precipitate formed
  2. filtrationfiltered
  3. customdried
  4. customFurther purification
  5. additionthe fractions containing the product

Sources & evidence

ORD record
ord-645f55898c594f5aa4a73c9373f636fb
Source dataset
uspto-grants-2009_09
Patent number
US07582625B2

Reaction notes

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