Ammonia → HCID 51340398, compound

HRID 1927799Notes

Reaction equation

HRID 1927799 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]([OH:15])=O)[CH2:11][S:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O[N:18]1C2C=CC=CC=2N=N1.O.N>C(Cl)Cl.CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]([NH2:18])=[O:15])[CH2:11][S:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 688405(4R)-3-[(tert-butoxy)carbonyl]-1,3-thiazolidine-4-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 51340398HCID 51340398, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

(4R)-3-(tert-Butyloxycarbonyl)thiazolidine-4-carboxylic acid (12.5 g, 54.1 mmol) was dissolved in CH2Cl2/DMF (9:1, 150 ml). To this solution at 0° C. was added 1-hydroxybenzotriazole hydrate (14.6 g, 108 mmol) and water-soluble carbodiimide (13.0 g, 65 mmol). After 1 h at 0° C. ammonia (35%, 50 ml) was added. After 18 h at 0° C. to room temperature the solvent was removed in vacuo and the residue was taken up in ethyl acetate (500 ml). This solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (eluant: 2% methanol, 98% chloroform) to give a colourless oil identified as the title compound (8.9 g, 38.4 mmol, 71%).

Workup

  1. customAfter 18 h at 0° C. to room temperature the solvent was removed in vacuo
  2. washThis solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (eluant: 2% methanol, 98% chloroform)
  6. customto give a colourless oil

Sources & evidence

ORD record
ord-b2e33ba101934037b8e7461302f3475d
Source dataset
uspto-grants-2012_05
Patent number
US08183280B2

Reaction notes

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