Hydrochloric Acid → HCID 66783219, compound

HRID 1096199Notes

Reaction equation

HRID 1096199 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C@@H:4]([NH:15][CH2:16][CH2:17][N:18]([CH2:27][CH2:28][C:29]([OH:31])=O)[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)[CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.C(N(CC)CC)C.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:32])[C@@H:4]([N:15]1[C:29](=[O:31])[CH2:28][CH2:27][N:18]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[CH2:17][CH2:16]1)[CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66782708HCID 66782708, compound

Product 1

HCID 66783219HCID 66783219, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8.20 g (15.77 mmol) of (S)-4-benzyloxy-2-{2-[(2-carboxy-ethyl)-(3,4-dichloro-phenyl)-amino]-ethylamino}-butyric acid methyl ester; HCl in 130 ml CH2Cl2 was treated with 2.20 (15.77 mmol) of triethylamine and at 0° C. with 3.70 g (18.93 mmol) of EDCI. The cooling bath was allowed to come to RT and after 15 h the reaction was extracted with aq. 10% KHSO4/Et2O (3×). The organic phases were washed with aq 10% KHSO4. solution, 10% NaCl and dried over Na2SO4 and purified by flash silica gel column (n-heptane:EtOAc 75:25 to 1:1) to yield 5.64 g (77%) of the title compound as a light yellow oil. MS: 465.1 (MH+, 2Cl).

Workup

  1. extractionthe reaction was extracted with aq. 10% KHSO4/Et2O (3×)
  2. washThe organic phases were washed with aq 10% KHSO4
  3. dry with materialsolution, 10% NaCl and dried over Na2SO4
  4. custompurified by flash silica gel column (n-heptane:EtOAc 75:25 to 1:1)

Sources & evidence

ORD record
ord-e645d978596e496cbe6aeaad1787b363
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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