Hydrochloric Acid → HCID 53986628, compound

HRID 1080842Notes

Reaction equation

HRID 1080842 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH2:13].ON1[C:19]2[CH:20]=[CH:21][CH:22]=C[C:18]=2[N:17]=N1.Cl.CN1C[CH2:30][O:29]CC1>CN(C=O)C.O>[CH3:30][O:29][C:22](=[O:13])[C@@H:21]1[CH2:20][CH2:19][CH2:18][N:17]1[C:10](=[O:12])[CH2:9][NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 53986628HCID 53986628, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-BOC-glycine (150 mmol) in DMF (250 mL) at 0° C., is added proline methyl ester. HCl (150 mmol), 1-hydroxybenzotriazole hydrate (22.2 g, 0.164 mmol), ethyl-3-(3-dimethylamino)propyl carbodiimide.HCl (31.4 g, 0.164 mmol) and 4-methylmorpholine (22.6 g, 0.224 mmol). The reaction mixture is stirred for 12 h while allowing the reaction to warm to room temperature. The reaction mixture is poured in water (750 mL) and extracted with ethyl acetate (2×150 mL). The combined organic extracts are washed as follows: KHSO4 (0.25M, 2×50 mL), water (1×50 mL), saturated aqueous NaHCO3 (2×50 mL) and saturated NaCl (1×50 mL). The organic layer is dried over MgSO4, filtered and the solvent removed in vacuo to give title compound.

Workup

  1. customthe reaction
  2. extractionextracted with ethyl acetate (2×150 mL)
  3. washThe combined organic extracts are washed
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-9ab2155ce61f4c0282a528f8b3afc3fc
Source dataset
uspto-grants-1996_12
Patent number
US05583146

Reaction notes

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