1,2-Dichloroethane → HCID 66807251, compound

HRID 574150Notes

Reaction equation

HRID 574150 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH3:34][O:35][CH2:36][CH2:37][NH2:38]>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])[C:10]([NH:38][CH2:37][CH2:36][O:35][CH3:34])=[O:12])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 80182-MethoxyethylamineHCID 757711-HydroxybenzotriazoleHCID 2756779N-Boc-(2'-Chlorophenyl)glycine

Product 1

HCID 66807251HCID 66807251, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 250 mg (0.88 mmol) of [(tert-butoxycarbonyl)amino](2-chlorophenyl)acetic acid, 177 mg (1.31 mmol) of HOBt, 252 mg (1.31 mmol) of EDC and 72 mg (0.96 mmol) of 2-methoxyethanamine in 6.3 ml of DMF was stirred at RT for 2 h. For purification, 1 ml of 1N hydrochloric acid was added and the entire reaction mixture was separated by preparative HPLC [Method 6]. The appropriate fraction was concentrated on a rotary evaporator and the residue was dried under high vacuum. This gave 269 mg (90% of theory) of the title compound.

Workup

  1. customFor purification, 1 ml of 1N hydrochloric acid
  2. additionwas added
  3. customthe entire reaction mixture
  4. customwas separated by preparative HPLC [Method 6]
  5. concentrationThe appropriate fraction was concentrated on a rotary evaporator
  6. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-286602afcfd44825ac5a676a9c47b5fe
Source dataset
uspto-grants-2015_05
Patent number
US09034855B2

Reaction notes

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