1,2-Dichloroethane → HCID 58333391, compound

HRID 2066843Notes

Reaction equation

HRID 2066843 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([CH2:28][OH:29])=[CH:23][C:22]=3[F:30])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[C:31]([O:35][C:36]([NH:38][CH2:39][C:40](O)=[O:41])=[O:37])([CH3:34])([CH3:33])[CH3:32].C(Cl)CCl.[C+](=O)C1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([CH2:28][O:29][C:40](=[O:41])[CH2:39][NH:38][C:36]([O:35][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:37])=[CH:23][C:22]=3[F:30])[CH2:19][CH2:20]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 78288N-(tert-butoxycarbonyl)glycineHCID 5325558HCID 5325558, compoundHCID 58333373HCID 58333373, compound

Product 1

HCID 58333391HCID 58333391, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Compound 10-1 (40 mg, 0.094 mmol), tert-butoxycarbonylamino-acetic acid (17 mg, 0.097 mmol), DMAP (3 mg, 0.024 mmol), EDC(22 mg, 0.11 mmol) and DCM (1 mL) were combined in that order and the reaction mixture was stirred for 20 h. The mixture was then washed with aqueous NaHCO3 (1 mL), concentrated under a stream of nitrogen and purified by Jones flash LC(eluent: 10-40% ethyl acetate+0.1% triethylamine in hexanes) to afford 12-1: LC-MS 408.2 (benzylium fragment).

Workup

  1. washThe mixture was then washed with aqueous NaHCO3 (1 mL)
  2. concentrationconcentrated under a stream of nitrogen
  3. custompurified by Jones flash LC(eluent
  4. custom10-40% ethyl acetate+0.1% triethylamine in hexanes) to afford 12-1

Sources & evidence

ORD record
ord-123b0e1df30b4c7ab70811e38c746728
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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