Triethylamine → HCID 57832551, compound

HRID 730686Notes

Reaction equation

HRID 730686 reaction equation
[N:1]1([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3][CH2:2]1.[O:20]=[C:21]1[N:27]([CH:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][C@@H:37]([C:48](O)=[O:49])[CH2:38][C:39]3[CH:44]=[C:43]([CH3:45])[C:42]([OH:46])=[C:41]([CH3:47])[CH:40]=3)=[O:35])[CH2:30][CH2:29]2)[CH2:26][CH2:25][C:24]2[CH:51]=[CH:52][CH:53]=[CH:54][C:23]=2[NH:22]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:20]=[C:21]1[N:27]([CH:28]2[CH2:29][CH2:30][N:31]([C:34]([O:36][C@H:37]([CH2:38][C:39]3[CH:40]=[C:41]([CH3:47])[C:42]([OH:46])=[C:43]([CH3:45])[CH:44]=3)[C:48]([N:17]3[CH2:16][CH2:15][CH:14]([N:1]4[CH2:2][CH2:3][CH:4]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:6]4)[CH2:19][CH2:18]3)=[O:49])=[O:35])[CH2:32][CH2:33]2)[CH2:26][CH2:25][C:24]2[CH:51]=[CH:52][CH:53]=[CH:54][C:23]=2[NH:22]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57807712HCID 57807712, compoundHCID 67273812HCID 67273812, compound

Product 1

HCID 57832551HCID 57832551, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

410 mg (1.20 mmol) ethyl 3-[1,4′]bipiperidinyl-4-yl-propionate (used as the bis-hydrochloride salt) were added at RT to a solution of 500 mg (1.04 mmol) (R)-2-(4-hydroxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate (Example 1h), 385 mg (1.20 mmol) TBTU and 0.48 mL (3.40 mmol) triethylamine in 10 mL DMF and the mixture was stirred for 2 h. The reaction mixture was purified by HPLC without any further working up. The fractions containing the product were combined, concentrated by evaporation i. vac. and the residue was stirred with saturated NaHCO3 solution.

Workup

  1. customThe reaction mixture was purified by HPLC without
  2. additionThe fractions containing the product
  3. concentrationconcentrated by evaporation i
  4. stirringand the residue was stirred with saturated NaHCO3 solution

Sources & evidence

ORD record
ord-8ab36ed463494e458a2cccd9b0a8fe0d
Source dataset
uspto-grants-2009_09
Patent number
US07582625B2

Reaction notes

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