1,2-Dichloroethane → HCID 58333428, compound

HRID 2066850Notes

Reaction equation

HRID 2066850 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]([C:28](O)=[O:29])=[CH:23][C:22]=3[F:31])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH3:32]OC(=O)CN.C1C=C[C:41]2[N:46](O)N=[N:44][C:42]=2C=1.C(Cl)CCl>C(Cl)Cl>[CH:1]([O:4][C:5]([N:7]1[CH2:8][CH2:9][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]([C:28](=[O:29])[NH:46][CH2:41][CH2:42][NH:44][CH3:32])=[CH:23][C:22]=3[F:31])[CH2:19][CH2:20]2)[CH2:11][CH2:12]1)=[O:6])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 69221Glycine methyl esterHCID 757711-HydroxybenzotriazoleHCID 58333593HCID 58333593, compound

Product 1

HCID 58333428HCID 58333428, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9-1 (32 mg, 0.073 mmol), amino-acetic acid methyl ester (0.11 mmol) and HOBT (15 mg, 0.11 mmol) were combined in DCM (1 mL) and stirred at room temperature for 10 minutes. EDC(19 mg, 0.1 mmol) was added and the mixture was stirred for 18 h. The solution was washed with 2 mL of aqueous NaHCO3, concentrated and taken up with 1 mL of DCM. 1 mL of TFA was added and the mixture was stirred at room temperature for 1 h. It was then concentrated under a stream of nitrogen and purified on preparative HPLC to give 31-1: LC-MS 496.5 (MH).

Workup

  1. stirringthe mixture was stirred for 18 h
  2. washThe solution was washed with 2 mL of aqueous NaHCO3
  3. concentrationconcentrated
  4. addition1 mL of TFA was added
  5. stirringthe mixture was stirred at room temperature for 1 h
  6. concentrationIt was then concentrated under a stream of nitrogen
  7. custompurified on preparative HPLC
  8. customto give 31-1

Sources & evidence

ORD record
ord-aad03f2391444b89879c616189bea6c2
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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