Lithium Hydroxide → HCID 87057945, compound

HRID 2279275Notes

Reaction equation

HRID 2279275 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([S:14][CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:12][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([S:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:12][N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 87057939HCID 87057939, compound

Product 1

HCID 87057945HCID 87057945, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Methyl 3-[2-(tert-butoxycarbonylamino)thiazol-5-yl]sulfanylpropanoate (9.0 g, 28.3 mmol) was dissolved in THF/H2O (3:1, 200 ml) and LiOH (1.4 g, 57.0 mmol) and the reaction mixture stirred at ambient temperature for 18 hours. The solvent was evaporated under vacuum then diluted with water and acidified with 1 M HCl to pH (4˜5). The solid formed was filtered, and washed with water and dried to give the title compound as a yellow solid (7.0 g, 80% yield) 1H NMR (400 Mz, CDCl3) δ1.57 (s, 9H), 2.69 (t, 2H), 2.98 (t, 2H), 7.33 (s, 1H).

Workup

  1. customThe solvent was evaporated under vacuum
  2. additionthen diluted with water
  3. customThe solid formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-52be84fcf6ca414d92ba0aec7ab301c0
Source dataset
uspto-grants-2015_09
Patent number
US09133218B2

Reaction notes

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