Ethylmorpholine → HCID 70037283, compound

HRID 987911Notes

Reaction equation

HRID 987911 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[NH2:6][CH:7]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:8]([OH:21])[CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH2:12][CH:11]1[C:18]([OH:20])=O.[C:29]([O:33][C:34]([NH:36][CH:37]([CH2:41][S:42][C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=1)[C:38](O)=[O:39])=[O:35])([CH3:32])([CH3:31])[CH3:30].C(N1CCOCC1)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C=O)C>[C:29]([O:33][C:34](=[O:35])[NH:36][CH:37]([C:38](=[O:39])[NH:6][CH:7]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:8]([OH:21])[CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH2:12][CH:11]1[C:18](=[O:20])[NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:41][S:42][C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=1)([CH3:30])([CH3:32])[CH3:31]

Participants

8

Reactant 5

HCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23256333HCID 23256333, compoundHCID 69854494HCID 69854494, compound

Product 1

HCID 70037283HCID 70037283, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

An ice-cooled mixture of 2-(3-amino-2-hydroxy-4-phenyl-butyl)-5-methoxy-cyclohexanecarboxylic acid tert-butylamine (93 mg, 0.247 mmol) and 2-tert-butoxycarbonylamino-3-(naphthalen-2-ylsulfanyl)-propionic acid (95 mg, 0.27 mmol) in dichloromethane (2 ml) and N,N′-dimethylformamide (1 ml) was treated sequentially with N-ethyl morpholine (144 μl, 1 mmol),1-hydroxybenzotriazole hydrate (57 mg, 0.31 mmol) and N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (63 mg, 0.30 mmol). The resulting mixture was allowed to warm to room temperature, stirred overnight and finally concentrated in vacuo. The residue was dissolved in ethyl acetate, washed sequentially with 5% aqueous sodium hydrogen carbonate solution, water, 2N hydrochloric acid and water. The organic phase was dried (anhydrous magnesium sulfate) and concentrated in vacuo to give, after purification by flash chromatography on silica gel (dichloromethane/methanol: 98/2), [1-[1-benzyl-3-(2-tert-butylcarbamoyl-4-methoxy-cyclohexyl)-2-hydroxy-propylcarbamoyl]-2-(naphthalen-2-ylsulfanyl)-ethyl]-carbamic acid tert-butyl ester (136 mg, 78%) as a white foam.

Workup

  1. concentrationfinally concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed sequentially with 5% aqueous sodium hydrogen carbonate solution, water, 2N hydrochloric acid and water
  4. dry with materialThe organic phase was dried (anhydrous magnesium sulfate)
  5. concentrationconcentrated in vacuo
  6. customto give
  7. customafter purification by flash chromatography on silica gel (dichloromethane/methanol: 98/2), [1-[1-benzyl-3-(2-tert-butylcarbamoyl-4-methoxy-cyclohexyl)-2-hydroxy-propylcarbamoyl]-2-(naphthalen-2-ylsulfanyl)-ethyl]-carbamic acid tert-butyl ester (136 mg, 78%) as a white foam

Sources & evidence

ORD record
ord-10c4dfb2709b42a18e38850aa19fd729
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

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