1,2-Dichloroethane → HCID 12069134, compound

HRID 1356205Notes

Reaction equation

HRID 1356205 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[C:8]([CH2:10][C@H:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:12]([OH:14])=O)[CH:7]=[CH:6][C:5]=1[O:23][CH2:24][C:25]([O:27][CH3:28])=[O:26].C(Cl)CCl.[CH3:34][O:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH2:41])=[CH:38][CH:37]=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[C:8]([CH2:10][C@H:11]([NH:15][C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[C:12](=[O:14])[NH:41][CH2:40][C:39]2[CH:42]=[CH:43][C:36]([O:35][CH3:34])=[CH:37][CH:38]=2)[CH:7]=[CH:6][C:5]=1[O:23][CH2:24][C:25]([O:27][CH3:28])=[O:26]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 754524-MethoxybenzylamineHCID 12069133HCID 12069133, compound

Product 1

HCID 12069134HCID 12069134, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-((2S)-2-tert-Butoxycarbonylamino-2-carboxy-ethyl)-2-methoxycarbonylmethoxy-benzoic acid methyl ester of Step F (51 mg, 0.12 mmol) is stirred in CH2Cl2 (1.2 mL) at 0° C. under N2. EDC (24 mg, 0.12 mmol) is added and the reaction mixture is stirred for and additional 10 minutes. 4-Methoxybenzyl amine (0.18 μl, 0.14 mmol) is then added and the reaction is allowed to warm to RT overnight. The reaction is diluted with CH2Cl2 (25 mL) and is subsequently washed with 2N HCl (2×25 mL) and then saturated NaHCO3 (2×25 mL). The organics are then dried over MgSO4, filtered and and purified by flash column chromatography to provide 5-[(2S)-2-tert-butoxycarbonylamino-2-(4-methoxy-benzylcarbamoyl)-ethyl]-2-methoxycarbonylmethoxy-benzoic acid methyl ester.

Workup

  1. washis subsequently washed with 2N HCl (2×25 mL)
  2. dry with materialThe organics are then dried over MgSO4
  3. filtrationfiltered
  4. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-37df71ca15b546908af6e7f56e4b3300
Source dataset
uspto-grants-2003_07
Patent number
US06586467B2

Reaction notes

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