4-Methylmorpholine → HCID 10175435, compound

HRID 722252Notes

Reaction equation

HRID 722252 reaction equation
[NH2:1][CH:2]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:17]([O:24][CH2:25][CH:26]([NH:30][C:31]([O:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1)=[O:32])[C:27](O)=[O:28])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1>CN(C=O)C>[CH2:17]([O:24][CH2:25][CH:26]([NH:30][C:31]([O:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1)=[O:32])[C:27]([NH:1][CH:2]([C:9]1[CH:10]=[C:11]([Cl:16])[CH:12]=[C:13]([Cl:15])[CH:14]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:28])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2758791HCID 2758791, compoundHCID 21884082HCID 21884082, compound

Product 1

HCID 10175435HCID 10175435, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

119.44 mg of ethyl 3-amino-3-(3,5-dichlorophenyl)propionate, 0.164 g of 3-benzyloxy-2-[3-(pyridin-2-ylamino)propoxycarbonylamino]propionic acid, 10.00 ml of DMF, 0.084 g of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 0.097 ml of 4-methylmorpholine are reacted together with stirring firstly for 1.5 hours at 50° C. and subsequently overnight at room temperature. After removal of the DMF by distillation, the residue is taken up in ethyl acetate, washed with water, evaporated to dryness and purified by chromatography over a short silica column (eluent ethyl acetate), giving ethyl 3-{3-benzyloxy-2-[3-(pyridin-2-ylamino)propoxycarbonylamino]propanoylamino}-3-(3,5-dichlorophenyl)propionate, RT 1.552 min, FAB-MS (M+H)+ 618.

Workup

  1. customAfter removal of the DMF
  2. distillationby distillation
  3. washwashed with water
  4. customevaporated to dryness
  5. custompurified by chromatography over a short silica column (eluent ethyl acetate)

Sources & evidence

ORD record
ord-fb49fec9eb4945aca227e72625bf9b92
Source dataset
uspto-grants-2006_11
Patent number
US07138417B2

Reaction notes

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