1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68744537, compound

HRID 2381024Notes

Reaction equation

HRID 2381024 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:17](O)=[O:18])=[CH:11][C:10]=1[OH:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[CH2:30][N:31]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.CN.C(N(CC)C(C)C)(C)C>CN(C=O)C.O.C(OCC)(=O)C>[C:24]([O:23][C:21](=[O:22])[NH:20][C@H:16]([C:17](=[O:18])[NH:31][CH3:30])[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([OH:28])[CH:11]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 10524262HCID 10524262, compound

Product 1

HCID 68744537HCID 68744537, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-3-(4-benzyloxy-3-hydroxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid (1.23 mmol) was dissolved in DMF (5 ml). EDCI (2 mmol) was added followed by HOBT (1 mmol) and methylamine hydrochloride (2 mmol). N,N-Diisopropylethylamine (2 mmol) was added and the solution was stirred at room temperature for 5 hours. The solution was diluted with water and ethyl acetate. The ethyl acetate extract was washed with dil HCl, with water and with brine. Drying (MgSO4) and evaporation gave the crude product which crystallised from ethyl acetate-hexane (1:1). [(S)-2-(4-Benzyloxy-3-hydroxy-phenyl)-1-methylcarbamoyl-ethyl]-carbamic acid tert-butyl ester was obtained as a white solid, 348 mg; HPLC/MS retention time 5.22 min, m/z 401 (MH+).

Workup

  1. extractionThe ethyl acetate extract
  2. washwas washed with dil HCl, with water and with brine
  3. customDrying
  4. custom(MgSO4) and evaporation
  5. customgave the crude product which
  6. customcrystallised from ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-97208c7bb678400ea33018ed59f9196c
Source dataset
uspto-grants-2012_09
Patent number
US08258097B2

Reaction notes

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