Sodium triacetoxyborohydride → HCID 11585460, compound

HRID 2193568Notes

Reaction equation

HRID 2193568 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([O:18][C:19](=[O:33])[NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:14][CH2:13]1)=[O:9].[CH3:34][N:35]([CH3:49])[CH2:36][CH2:37][CH2:38][O:39][C:40]1[CH:45]=[CH:44][C:43]([CH2:46]C=O)=[CH:42][CH:41]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO>[CH3:49][N:35]([CH3:34])[CH2:36][CH2:37][CH2:38][O:39][C:40]1[CH:41]=[CH:42][C:43]([CH2:46][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([O:18][C:19](=[O:33])[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:16][CH2:17]2)=[O:9])=[CH:44][CH:45]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 68525725HCID 68525725, compoundHCID 86607676HCID 86607676, compound

Product 1

HCID 11585460HCID 11585460, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Biphenyl-2-ylcarbamic acid 1-[2-(5-aminopentylcarbamoyl)ethyl]piperidin-4-yl ester (45.2 mg, 0.1 mmol; prepared as described in Preparation 4) was dissolved in 1 mL of MeOH. To the solution was added [4-(3-dimethylaminopropoxy)phenyl]acetaldehyde (0.1 mmol) at room temperature. The reaction was stirred at room temperature for 30 minutes before it was treated with Na(OAc)3BH (64 mg, 0.3 mmol). Stirring was continued for an additional 1 hour. The reaction mixture was concentrated, then dissolved in 1 mL of 1:1 HOAc/H2O solution and purified on reverse phase HPLC. The title compound was obtained as a tri(trifluoroacetate) salt. MS m/z: [M+H+] calcd for C38H53N5O4, 644.42; found, 644.3.

Workup

  1. stirringStirring
  2. waitwas continued for an additional 1 hour
  3. concentrationThe reaction mixture was concentrated
  4. dissolutiondissolved in 1 mL of 1:1 HOAc/H2O solution
  5. custompurified on reverse phase HPLC

Sources & evidence

ORD record
ord-5759e2a59628451ebc49272aff7b2e78
Source dataset
uspto-grants-2012_12
Patent number
US08329911B2

Reaction notes

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