Morpholine → HCID 67196886, compound

HRID 1893832Notes

Reaction equation

HRID 1893832 reaction equation
Br[CH:2]([CH2:25][CH3:26])[CH2:3][CH2:4][CH2:5][N:6]([C@H:17]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:18]([NH2:20])=[O:19])[S:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8].CCN(CC)CC.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>C(Cl)Cl>[O:37]1[CH2:38][CH2:39][N:34]([CH:2]([CH2:25][CH3:26])[CH2:3][CH2:4][CH2:5][N:6]([C@H:17]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:18]([NH2:20])=[O:19])[S:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:35][CH2:36]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 67195389HCID 67195389, compound

Product 1

HCID 67196886HCID 67196886, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2R)-2-[N-(4-bromohexyl)-N-(4-chlorobenzenesulfonyl)amino]-4-methylpentanoic acid amide (Example 24; prepared as described in Reaction Scheme 1; 0.20 g, 0.44 mmol), Et3N (0.25 mL, 1.7 mmol), and morpholine (150 mg, 1.7 mmol) in CH2Cl2 (2 mL) was stirred at rt for 18 h. The reaction was then concentrated to give a crude white wax which was purified by flash chromatography (SiO2, 85% EtOAc/5% hexanes/10% MeOH) to afford the title compound (112 mg) as a white solid in 54% yield. MS (ESI), (M+H)+474.4; 1H NMR (DMSO-d6) δ 7.82 (d, 2H, J=8.0), 7.64 (d, 2H, J=8.0), 7.42 (br s, 1H) 6.99 (s, 1H), 4.25 (m, 1H), 3.51-3.60 (br s, 4H), 3.18-3.41 (m, 2H), 2.25-2.35 (br s, 4H), 2.27 (m, 2H) 1.15-1.62 (m, 9H), 0.80 (d, 6H, J=6.0).

Workup

  1. concentrationThe reaction was then concentrated
  2. customto give a crude white wax which
  3. customwas purified by flash chromatography (SiO2, 85% EtOAc/5% hexanes/10% MeOH)

Sources & evidence

ORD record
ord-7869455d35284fb28acea03c5ef1ee78
Source dataset
uspto-grants-2013_08
Patent number
US08513253B2

Reaction notes

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