Sodium Bicarbonate → HCID 57971697, compound

HRID 548266Notes

Reaction equation

HRID 548266 reaction equation
[CH2:1]([O:5][CH:6]([O:8][NH:9][C:10]([C:12]1[S:16][C:15]2[CH:17]=[C:18]([CH:21]=O)[CH:19]=[CH:20][C:14]=2[CH:13]=1)=[O:11])[CH3:7])[CH:2]([CH3:4])[CH3:3].[CH:23]1([O:28][C:29](=[O:48])[C@@H:30]([NH:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([CH2:46][NH2:47])=[CH:42][CH:41]=2)[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl.C(O)(=O)C>[CH:23]1([O:28][C:29](=[O:48])[C@@H:30]([NH:38][CH2:39][C:40]2[CH:41]=[CH:42][C:43]([CH2:46][NH:47][CH2:21][C:18]3[CH:19]=[CH:20][C:14]4[CH:13]=[C:12]([C:10](=[O:11])[NH:9][O:8][CH:6]([O:5][CH2:1][CH:2]([CH3:3])[CH3:4])[CH3:7])[S:16][C:15]=4[CH:17]=3)=[CH:44][CH:45]=2)[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57971602HCID 57971602, compoundHCID 57971713HCID 57971713, compound

Product 1

HCID 57971697HCID 57971697, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

6-formyl-benzo[b]thiophene-2-carboxylic acid (1-isobutoxy-ethoxy) amide (Scheme 7) (220 mg, 0.68 mmol) and (S)-2-(4-Aminomethyl-benzylamino)-3-phenyl-propionic acid cyclopentyl ester (263 mg, 0.75 mmol) were dissolved in DCE (10 mL) under an atmosphere of N2. Sodium triacetoxyborohydride (430 mg, 2.04 mmol) and acetic acid (50 μL) were added and the reaction stirred at r.t for 3 h. Sodium hydrogen carbonate (20 mL) was added and the reaction mixture extracted with dichloromethane (3×50 mL). The organic layers were combined and concentrated. The residue was purified by column chromatography (50%-100% EtOAc/heptane) to give the protected compound (80 mg, 21%). m/z 658 [M++H]+

Workup

  1. extractionthe reaction mixture extracted with dichloromethane (3×50 mL)
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography (50%-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-27d43f7d1d8f4af3ba1052c6ba0dba5c
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

Loading…