Ethanethiol → HCID 86641059, compound

HRID 1864487Notes

Reaction equation

HRID 1864487 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][CH2:18][SH:19].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH3:13])[C:14](=[O:16])[S:19][CH2:18][CH3:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 10868Dicyclohexylcarbodiimide2×HCID 736104N-carbobenzyloxyalanine

Product 1

HCID 86641059HCID 86641059, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

A 250 mL round bottom flask was charged with benzyloxy-carbonyl-L alanine (15.0 g, 67.2 mmol) and 67.2 mL of dichloromethane. To this mixture was added DMAP (0.82 g, 6.72 mmol) and chilled EtSH (0° C., 5.46 mL, 73.9 mmol) followed by the addition of DCC (15.2 g, 73.9 mmol) in one portion. The addition of the DCC is highly exothermic so the reaction will bubble upon addition, and the reaction should be kept well vented. The resulting mixture was stirred for 30 minutes at 22° C. The resulting white solid was then removed by vacuum filtration, and the filtrate was concentrated. Silica Gel chromatography using hexanes with polarization to 8:1 hexanes/ethyl acetate afforded 93% yield (18.0g, 62.5 mmol) of the desired product as a colorless oil.

Workup

  1. customis highly exothermic so the reaction
  2. customwill bubble upon addition
  3. customthe reaction
  4. customThe resulting white solid was then removed by vacuum filtration
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f4cf609a2d1240ab8d78244e631ec250
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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