Diisopropylcarbodiimide → HCID 86656466, compound

HRID 2040506Notes

Reaction equation

HRID 2040506 reaction equation
[NH2:1][C@@H:2]([CH2:7][CH2:8][S:9][CH3:10])[C:3]([O:5][CH3:6])=[O:4].[C:11]([NH:18][CH2:19][C:20](O)=[O:21])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(N=C=NC(C)C)(C)C.C(N(C(C)C)CC)(C)C>ClCCl>[CH3:15][C:14]([CH3:17])([CH3:16])[O:13][C:11](=[O:12])[NH:18][CH2:19][C:20](=[O:21])[NH:1][C@H:2]([C:3]([O:5][CH3:6])=[O:4])[CH2:7][CH2:8][S:9][CH3:10]

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 64684methyl (2S)-2-amino-4-(methylsulfanyl)butanoateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531Diisopropylethylamine

Product 1

HCID 86656466HCID 86656466, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-methyl 2-amino-4-(methylthio)butanoate (5 g, 30.7 mmol) and Boc-glycine (6.4 g, 36.8 mmol) in dichloromethane (100 mL) at room temperature was added diisopropylcarbodiimide (4.6 g, 36.8 mmol) and diisopropylethylamine (4.75 g, 36.8 mmol). The mixture was stirred overnight at room temperature, washed with 1N HCl, brine, and dried over sodium sulfate, filtered and concentrated to give a residue, which was purified on silica gel column to give (S)-methyl 12,12-dimethyl-7,10-dioxo-11-oxa-2-thia-6,9-diazatridecane-5-carboxylate (7 g, 71%). MS calcd for (C13H24N2O5S+H)+: 321.1; MS found: (M+H)+=321.2.

Workup

  1. washwashed with 1N HCl, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a residue, which
  6. customwas purified on silica gel column

Sources & evidence

ORD record
ord-bf6ae43ec3cb4a56b4680d9d9747a001
Source dataset
uspto-grants-2013_11
Patent number
US08580859B2

Reaction notes

Loading…