Ammonia → Tert-butyl 2-carbamoylthiomorpholine-4-carboxylate

HRID 57585Notes

Reaction equation

HRID 57585 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][S:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=[N:23]C=2C=1.CCN=C=NCCCN(C)C.Cl.N>CN(C=O)C.CCOC(C)=O>[C:14]([CH:10]1[S:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1)(=[O:16])[NH2:23]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27606194-(Tert-butoxycarbonyl)thiomorpholine-2-carboxylic acid

Product 1

HCID 71113884Tert-butyl 2-carbamoylthiomorpholine-4-carboxylateYield 99.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(tert-butoxycarbonyl)thiomorpholine-2-carboxylic acid (2.47 g, 10 mmol) and HOBt (1.62 g, 12 mmol) were dissolved in DMF (20 mL), and EDCl (2.11 g, 11 mmol) was added. The reaction mixture was stirred for 1 hour, and 25% aqueous ammonia (5 mL) was added, and the reaction was stirred for another 2 hours. The reaction was then diluted with EtOAc (200 mL) and partitioned with water (100 mL). The organic layer was washed with saturated aq. NaHCO3 (2×100 mL), and then dried with Na2SO4. The solvent was removed in vacuo to afford title compound as white solid 2.46 g. MS (m/z): 147 (M+H-Boc)+

Workup

  1. stirringthe reaction was stirred for another 2 hours
  2. custompartitioned with water (100 mL)
  3. washThe organic layer was washed with saturated aq. NaHCO3 (2×100 mL)
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ff71ed8537be415ba710f86e7b9acbb8
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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