Ethanethiol → HCID 86592555, compound

HRID 1433052Notes

Reaction equation

HRID 1433052 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH:16]([CH3:18])[CH3:17])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][CH2:20][SH:21].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:20]([S:21][C:13](=[O:15])[C@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH:16]([CH3:18])[CH3:17])[CH3:19]

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 10868DicyclohexylcarbodiimideHCID 712434N-alpha-Benzyloxycarbonyl-D-valine

Product 1

HCID 86592555HCID 86592555, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution containing (R)-2-benzyloxycarbonylamino-3-methyl-butyric acid (5.0 g, 20.0 mmol) in anhydrous CH2Cl2 (20 mL) is added DMAP (258 mg, 2.0 mmol) followed by chilled EtSH (1.6 mL, 22.0 mmol). Dicyclohexylcarbodiimide (4.5 g, 22.0 mmol) is added in one portion and the reaction is complete after 30 min. The solid material is removed by vacuum filtration and the filtrate is concentrated. The crude product is purified by flash silica gel chromatography (hexane to 8:1 hexane/EtOAc) to provide (R)-2-benzyloxycarbonylamino-3-methyl-thiobutyric acid S-ethyl ester (5.21 g, 88%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ0.85 (d, J=6.8 Hz, 3H), 0.98 (d, J=6.8 Hz, 3H), 1.23 (t, J=7.5 Hz, 3H), 2.27 (m, 1H), 2.88 (q, J=7.5 Hz, 2H), 4.35 (dd, J=9.5, 4.6 Hz, 1H), 5.13 (s, 2H), 5.25 (br d, J=9.5 Hz, 1H), 7.30-7.36 (m, 5H) ppm.

Workup

  1. customThe solid material is removed by vacuum filtration
  2. concentrationthe filtrate is concentrated
  3. customThe crude product is purified by flash silica gel chromatography (hexane to 8:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-ebb42276080d4865a6e3119883f02ce6
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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