Sodium borohydride → 1-(2-{[6-({5-[{2-([tert-Butoxycarbonyl)(methyl)amino]ethyl}(methyl)carbamoyl]-4-methylthiophen-2-yl}amino)hexanoyl](methyl)amino}ethyl)piperidin-4-yl biphenyl-2-ylcarbamate

HRID 446586Notes

Reaction equation

HRID 446586 reaction equation
[C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:28])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([CH3:27])[C:19](=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=O)[CH2:12][CH2:11]1.[NH2:35][C:36]1[S:40][C:39]([C:41]([N:43]([CH3:55])[CH2:44][CH2:45][N:46]([CH3:54])[C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:42])=[C:38]([CH3:56])[CH:37]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[BH4-].[Na+]>C(Cl)Cl.C(O)(=O)C>[C:1]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:28])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([C:19](=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:35][C:36]2[S:40][C:39]([C:41](=[O:42])[N:43]([CH2:44][CH2:45][N:46]([C:47]([O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:53])[CH3:54])[CH3:55])=[C:38]([CH3:56])[CH:37]=2)[CH3:27])[CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 4311764Sodium borohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 86663471tert-Butyl (2-{[(5-amino-3-methylthiophen-2-yl)carbonyl](methyl)amino}ethyl)methylcarbamateHCID 867619011-{2-[Methyl(6-oxohexanoyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate

Product 1

HCID 666713931-(2-{[6-({5-[{2-([tert-Butoxycarbonyl)(methyl)amino]ethyl}(methyl)carbamoyl]-4-methylthiophen-2-yl}amino)hexanoyl](methyl)amino}ethyl)piperidin-4-yl biphenyl-2-ylcarbamateYield 49%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

The compound (210 mg, 0.450 mmol) obtained in Example 4g and the compound (134 mg, 0.409 mmol) obtained in Example 89c were dissolved in methylene chloride (4 mL), acetic acid (79 μL) and sodium triacetoxyborohydride (130 mg, 0.614 mmol) were added, and the mixture was stirred at room temperature for 12 hours. Sodium borohydride (16 mg, 0.409 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1→ethyl acetate:methanol=50:1, v/v) to give the title compound (153 mg; yield, 49%) as a light yellow solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customThe solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1→ethyl acetate:methanol=50:1, v/v)

Sources & evidence

ORD record
ord-1fe3fcd2ecc342ee8f66a044b98d8a4d
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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