Triethylamine → HCID 178472032, compound

HRID 1063651Notes

Reaction equation

HRID 1063651 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]([N:9]([CH3:21])[CH2:10][CH2:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([OH:20])=O)[CH2:14][CH2:13]2)=[O:8])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH2:30]([O:32][C:33](=[O:38])[CH2:34][CH2:35][NH:36][CH3:37])[CH3:31].CCN(CC)CC>C(Cl)Cl.CN(C=O)C>[CH2:30]([O:32][C:33](=[O:38])[CH2:34][CH2:35][N:36]([C:18]([C@H:15]1[CH2:14][CH2:13][C@H:12]([CH2:11][CH2:10][N:9]([C:7]([O:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:23][CH:22]=2)=[O:8])[CH3:21])[CH2:17][CH2:16]1)=[O:20])[CH3:37])[CH3:31]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 541480Ethyl 3-(methylamino)propanoateHCID 178483657HCID 178483657, compound

Product 1

HCID 178472032HCID 178472032, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.41 g (1.20 mmol) of trans-4-{2-[(4-chloro-phenoxycarbonyl)-methyl-amino]-ethyl}-cyclohexanecarboxylic acid in 12 mL of CH2Cl2 was treated at RT with 1 drop of DMF, followed by 0.11 mL (1.32 mmol, 1.1 eq) of oxalyl chloride within 5 min and stirring was continued for 90 min. The solution was evaporated and the residue was redissolved in 12 mL of CH2Cl2. At 0° C. this solution was added to a solution of 0.20 g (1.56 mmol, 1.3 eq) of 3-methylamino-propionic acid ethyl ester and 0.84 mL (6.00 mmol, 5 eq) of Et3N in 4 mL of CH2Cl2. The reaction mixture was kept at RT for 1.5 h, then the substance was partitioned between Et2O (×3)/aqueous 10% KHSO4. The organic phases were washed once with aqueous 10% NaCl, dried over Na2SO4 and evaporated to give 0.51 g (94%) of trans-3-[(4-{2-[(4-chloro-phenoxycarbonyl)-methyl-amino]-ethyl}-cyclohexanecarbonyl)-methyl-amino]-propionic acid ethyl ester, MS: 453 (MH+, 1Cl).

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue was redissolved in 12 mL of CH2Cl2
  3. waitThe reaction mixture was kept at RT for 1.5 h
  4. customthe substance was partitioned between Et2O (×3)/aqueous 10% KHSO4
  5. washThe organic phases were washed once with aqueous 10% NaCl
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-5902456c1d164848b4f14b03ea0955ee
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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