Dimethylformamide → HCID 22870564, compound

HRID 975808Notes

Reaction equation

HRID 975808 reaction equation
Cl.[NH2:2][C@@H:3]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)[C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]=2[O:5][CH2:4]1.[CH2:25]([O:27][C:28](=[O:51])[C@H:29](OS(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O)[CH2:30][CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[CH3:26].CN1CCOCC1.CN(C)C=O>CCCCCC.C(OCC)(=O)C>[CH2:25]([O:27][C:28]([C@@H:29]([NH:2][C@@H:3]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)[C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]=2[O:5][CH2:4]1)[CH2:30][CH2:31][CH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1)=[O:51])[CH3:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 54177175HCID 54177175, compoundHCID 67713888HCID 67713888, compound

Product 1

HCID 22870564HCID 22870564, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

1.5 g of (S)-3-amino-4-oxo-5-(p-isopropylbenzyl)-2,3,4,5-tetrahydro-1,5-benzoxazepine hydrochloride, 2.93 g of (R)-alpha-[[(4-nitrophenyl)sulfonyl]oxy]-4-cyclohexylbutyric acid ethyl ester (Helv. Chim. Acta 71 (2), 337, 1988), 1.85 ml of N-methylmorpholine and 2 ml of dimethylformamide are heated at 75° C. for 3 days. The reaction mixture is concentrated and separated by means of flash chromatography (230 g of silica gel, eluant hexane/ethyl acetate 4:1). The product is obtained in the form of a colourless resin. Rf value (eluant hexane/ethyl acetate 4:1): 0.36.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customseparated by means of flash chromatography (230 g of silica gel, eluant hexane/ethyl acetate 4:1)
  3. customThe product is obtained in the form of a colourless resin

Sources & evidence

ORD record
ord-ed9ca0fd4fdc4f18b07051fa79ef9e20
Source dataset
uspto-grants-1997_03
Patent number
US05610153

Reaction notes

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