Triethylamine → 4-(4-{[(S)-2-(4-methanesulfonyl-phenyl)-1-methylethyl]propylamino}butyl)-3-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 10198Notes

Reaction equation

HRID 10198 reaction equation
Cl.[CH2:2]([NH:5][C@@H:6]([CH3:18])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[CH2:3][CH3:4].[C:19]([O:23][C:24]([N:26]1[CH2:32][CH2:31][CH2:30][N:29]([CH2:33][CH2:34][CH2:35][CH:36]=O)[C:28](=[O:38])[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:19]([O:23][C:24]([N:26]1[CH2:32][CH2:31][CH2:30][N:29]([CH2:33][CH2:34][CH2:35][CH2:36][N:5]([C@@H:6]([CH3:18])[CH2:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4])[C:28](=[O:38])[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 69223624[(S)-2-(4-methanesulfonylphenyl)-1-methylethyl]-propylamine hydrochlorideHCID 865841633-Oxo-4-(4-oxobutyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 692253654-(4-{[(S)-2-(4-methanesulfonyl-phenyl)-1-methylethyl]propylamino}butyl)-3-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of propyl-[(S)-2-(4-methanesulfonylphenyl)-1-methylethyl]-amine hydrochoride (0.50 g, 1.7 mmole), 3-oxo-4-(4-oxobutyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (0.5 g, 1.76 mmole), triethylamine (0.24 mL, 1.7 mmole), and sodium triacetoxyborohydride (0.54 g, 2.6 mmole) in 1,2-dichloroethane (20 mL) was stirred at room temperature for 17 hours. The solvent was removed, and the residue was partitioned between ethyl acetate (30 mL) and 5% sodium carbonate (20 mL). The organic phase was dried (magnesium sulfate) and concentrated to give 4-(4-{[(S)-2-(4-methanesulfonyl-phenyl)-1-methylethyl]propylamino}butyl)-3-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester, (0.89 g), as a syrup. Nmr (chloroform-d) δ (ppm): 0.82, t, 3H; 0.94, d, 3H; 1.46, s, 9H; 3.05, s, 3H; 7.36, d, 2H; 7.83, d, 2H.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate (30 mL) and 5% sodium carbonate (20 mL)
  3. dry with materialThe organic phase was dried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ddc8884c55174314b2e54eb7f87c5faf
Source dataset
uspto-grants-2006_08
Patent number
US07094778B2

Reaction notes

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