Triethylamine → HCID 22855123, compound

HRID 1755823Notes

Reaction equation

HRID 1755823 reaction equation
Cl.[NH2:2][C@@H:3]([C:5]([NH2:7])=[O:6])[CH3:4].[C:8]([O:12][C:13](=[O:30])[C@H:14]([CH3:29])[N:15]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[CH2:16][CH:17]=O)([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C.C([BH3-])#N.[Na+]>CO>[C:8]([O:12][C:13](=[O:30])[C@H:14]([CH3:29])[N:15]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[CH2:16][CH2:17][NH:2][C@@H:3]([C:5]([NH2:7])=[O:6])[CH3:4])([CH3:9])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2775814(2R)-2-Aminopropanamide hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 22855124HCID 22855124, compound

Product 1

HCID 22855123HCID 22855123, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The D-alanine amide hydrochloride, (45) (2.5 g) (20.18 mmol) was dissolved in methanol, followed by the aldehyde (44) (3.30 g, 10.27 mmol) and triethylamine (1.40 mL, 1.0 g, 10.07 mmol). Sodium cyanoborohydride (0.86 g, 13.7 mmol) was added and the solution was kept stirring at room temperature overnight. The solution was evaporated under vacuum. The residue was taken up in chloroform:methanol (98:2) and flash chromatographed silica gel to yield the titled product (46): (2.48 g, 61%). 1H-NMR CDCl3) δ7.33 (s, 5H), 6.00 (br s, 1H), 5.20 (d, 2H), 4.67-3.00 (m, 4H), 2.77 (t, 2H), 1.83-1.23 (s/m, 13H).

Workup

  1. customThe solution was evaporated under vacuum
  2. customflash chromatographed silica gel

Sources & evidence

ORD record
ord-db0e006624764fa3b6ba333d357c5b03
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

Loading…