1,2-Dichloroethane → Boc-Cys(StBu)-Gly-OCH3

HRID 1055261Notes

Reaction equation

HRID 1055261 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][S:4][S:5][C:6]([CH3:9])([CH3:8])[CH3:7].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.Cl.[CH3:42][O:43][C:44](=[O:47])[CH2:45][NH2:46]>ClCCl.CCOC(C)=O>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([NH:46][CH2:45][C:44]([O:43][CH3:42])=[O:47])=[O:12])[CH2:3][S:4][S:5][C:6]([CH3:7])([CH3:8])[CH3:9]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 122755Glycine methyl ester hydrochlorideHCID 14258343N-((1,1-dimethylethoxy)carbonyl)-3-((1,1-dimethylethyl)dithio)-L-alanine

Product 1

HCID 14334607Boc-Cys(StBu)-Gly-OCH3Yield 89%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Boc-Cys(StBu)-OH 9 (1.00 g, 3.23 mmol) was dissolved in dry dichloromethane (25 mL) followed by the addition of EDC (0.75 g, 3.87 mmol), HOBt (0.53 g, 3.87 mmol), NMM (1.77 mL, 16.15 mmol) and glycine methyl ester hydrochloride (0.61 g, 4.84 mmol) at 0° C. under argon. The reaction mixture was then allowed to warm to room temperature and stirred overnight. After evaporation of solvent, the residue obtained was taken in EtOAc (35 mL), washed with 20% citric acid solution (2 30 mL), sat. NaHCO3 (20 mL), brine and dried over MgSO4. The EtOAc layer was evaporated in vacuo and resulting crude product was purified by flash silica gel column chromatography to get the dipeptide product 12 as white foam (1.09 g, 89% yield). 1H NMR (300 MHz, CDCl3) δ7.35, 5.81 (2H), 4.44 (1H), 3.82 (2H), 3.61 (3H), 3.02-2.83 (2H), 1.43, 1.28 (18H); 13C NMR (75 MHz, CDCl3) δ171.2, 169.9, 155.5, 80.0, 53.5, 52.3, 48.0, 41.4, 37.9, 30.0, 28.5; ESI-LRMS m/z 380.5 (M+H)+.

Workup

  1. customAfter evaporation of solvent
  2. customthe residue obtained
  3. washwashed with 20% citric acid solution (2 30 mL), sat. NaHCO3 (20 mL), brine
  4. dry with materialdried over MgSO4
  5. customThe EtOAc layer was evaporated in vacuo
  6. customresulting crude product
  7. customwas purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-287a9219e46348b59c5236a34e0ee9c6
Source dataset
uspto-grants-2016_07
Patent number
US09394338B2

Reaction notes

Loading…