Diisopropylethylamine → HCID 86590131, compound

HRID 1840518Notes

Reaction equation

HRID 1840518 reaction equation
[CH3:1][C:2]([CH3:31])([O:4][C:5]([NH:7][C@@H:8]([CH2:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:17][CH2:16]1)[C:9]([OH:11])=O)=[O:6])[CH3:3].Cl.[CH2:33]([CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)[CH3:34].C(N(CC)C(C)C)(C)C>ClCCl.C(OCC)(=O)C>[CH3:31][C:2]([CH3:1])([O:4][C:5]([NH:7][C@H:8]([C:9]([N:38]1[CH2:39][CH2:40][CH:35]([CH2:33][CH3:34])[CH2:36][CH2:37]1)=[O:11])[CH2:12][CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17][N:18]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:19][CH2:20]1)=[O:6])[CH3:3]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 234481304-Ethylpiperidine--hydrogen chloride (1/1)HCID 69820413HCID 69820413, compound

Product 1

HCID 86590131HCID 86590131, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.7 g (4.4 mmol) of O-(benzotriazol-1-yl)-N,N,N,N′-tetramethyluronium hexafluorophosphate (HBTU) are added portionwise, at 0° C. under nitrogen, to a solution of 1.73 g (4.0 mmol) of (S)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-1-[(phenylmethoxy)carbonyl]-piperidine-4-pentanoic acid, 0.66 g (4.4 mmol) of 4-ethylpiperidine hydrochloride and 1.8 ml (10.4 mmol) of N,N-diisopropylethylamine (DIEA) in dichloromethane. The reaction mixture is allowed to warm slowly to room temperature and the reaction is continued for 18 hours. The reaction mixture is then taken up in 200 ml of ethyl acetate and is washed with 100 ml of 1N hydrochloric acid solution and then with 100 ml of saturated sodium hydrogen carbonate solution and with 100 ml of saturated sodium chloride solution. The resulting product is dried over sodium sulphate and is filtered and then concentrated. The residue obtained is purified by chromatography on a column of silica gel, eluting under pressure with a 4/6 ethyl acetate/cyclohexane mixture. 2 g of phenylmethyl (S)-4-[4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(4-ethylpiperid-1-yl)-5-oxopentyl]piperidine-1-carboxylate are obtained in the form of a viscous oil.

Workup

  1. washis washed with 100 ml of 1N hydrochloric acid solution
  2. dry with materialThe resulting product is dried over sodium sulphate
  3. filtrationis filtered
  4. concentrationconcentrated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica gel
  7. washeluting under pressure with a 4/6 ethyl acetate/cyclohexane mixture

Sources & evidence

ORD record
ord-f5ae52aabbe9478288dd1539f94be35a
Source dataset
uspto-grants-2004_01
Patent number
US06680329B2

Reaction notes

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