Ethylmorpholine → N-(cyclohexylglycyl-glutaminyl-serinyl)leucine benzyl ester hydrochloride

HRID 1267569Notes

Reaction equation

HRID 1267569 reaction equation
[ClH:1].[CH2:2]([O:9][C:10](=[O:32])[C@H:11]([CH2:28][CH:29]([CH3:31])[CH3:30])[NH:12][C:13](=[O:27])[C@H:14]([CH2:25][OH:26])[NH:15][C:16](=[O:24])[C@H:17]([CH2:19][CH2:20][C:21](=[O:23])[NH2:22])[NH2:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:33]1[CH:38]=[C:37]2N=N[N:41](O)[C:36]2=[CH:35][CH:34]=1.O.C(N1CC[O:49][CH2:48][CH2:47]1)C.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.C(OCC)(=O)C.O>[ClH:1].[CH2:2]([O:9][C:10](=[O:32])[C@H:11]([CH2:28][CH:29]([CH3:30])[CH3:31])[NH:12][C:13](=[O:27])[C@H:14]([CH2:25][OH:26])[NH:15][C:16](=[O:24])[C@H:17]([CH2:19][CH2:20][C:21](=[O:23])[NH2:22])[NH:18][C:48](=[O:49])[CH2:47][NH:41][CH:36]1[CH2:35][CH2:34][CH2:33][CH2:38][CH2:37]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69996228N-(glutaminyl-serinyl)leucine benzyl ester hydrochloride

Product 1

HCID 69994356N-(cyclohexylglycyl-glutaminyl-serinyl)leucine benzyl ester hydrochloride

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

N-(glutaminyl-serinyl)leucine benzyl ester hydrochloride (2.6 kg) (prepared as described in Step 3), N-Boc-L-cyclohexylglycine (1.414 kg) and HOBt hydrate (168 g) were dissolved in DMF (13.0 L). N-ethylmorpholine (1.266 kg, 11.0 M) and EDC hydrochloride (1.265 kg) were added and the mixture stirred at 20° C. for 3 hours. The solution was diluted with ethyl acetate (13.0 L) and water (26.0 L) added. The product precipitated and the slurry was stirred at room temperature for 1 hour. The solid was collected by filtration, washed with 1:1 ethyl acetate/water (60 L) dried on the filter under nitrogen for 24 hours and dried in vacuo at 45°. The title compound was obtained as a white solid.

Workup

  1. additionadded
  2. customThe product precipitated
  3. stirringthe slurry was stirred at room temperature for 1 hour
  4. filtrationThe solid was collected by filtration
  5. washwashed with 1:1 ethyl acetate/water (60 L)
  6. customdried on the
  7. filtrationfilter under nitrogen for 24 hours
  8. customdried in vacuo at 45°

Sources & evidence

ORD record
ord-b47cdf6dce524e43b881edd3d3fc367c
Source dataset
uspto-grants-2003_04
Patent number
US06552166B1

Reaction notes

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