N-methyl-2-pyrrolidone → (1-Methyl-2-oxo-2-thiomorpholin-4-yl-ethyl)-carbamic acid tert-butyl ester

HRID 77758Notes

Reaction equation

HRID 77758 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CN1C(=O)CCC1.CCN=C=NCCCN(C)C.[NH:42]1[CH2:47][CH2:46][S:45][CH2:44][CH2:43]1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([CH3:13])[C:10](=[O:12])[N:42]1[CH2:47][CH2:46][S:45][CH2:44][CH2:43]1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 13387N-methyl-2-pyrrolidoneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 67164ThiomorpholineHCID 757711-HydroxybenzotriazoleHCID 2684712-N-Boc-aminopropionic acid

Product 1

HCID 47289052(1-Methyl-2-oxo-2-thiomorpholin-4-yl-ethyl)-carbamic acid tert-butyl esterYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-tert-Butoxycarbonylamino-propionic acid (3.5 g, 18.5 mmol), HOBt (22.2 mmol), NMP (22.2 mmol) and EDCI (22.2 mmol) in CH2Cl2 was added thiomorpholine (2.29 g, 22.2 mmol) at 0° C. The reaction mixture was stirred at 0° C. overnight, then washed with 2% aqueous NaOH, water, brine, and dried over Na2SO4. The solvent was removed under vacuum to give (1-Methyl-2-oxo-2-thiomorpholin-4-yl-ethyl)-carbamic acid tert-butyl ester (5.0 g) yield 98%. MS (M+H)=275.

Workup

  1. washwashed with 2% aqueous NaOH, water, brine
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-f75de7be92384d01b93865bffc3338a8
Source dataset
uspto-grants-2014_09
Patent number
US08841336B2

Reaction notes

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