4-Methylmorpholine → 4-{2-[2-(S)-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-acetyl}-benzoic acid methyl ester

HRID 606588Notes

Reaction equation

HRID 606588 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12][NH2:13])=[CH:7][CH:6]=1.CCN=C=NCCCN(C)C.Cl.[C:28]([N:35]([CH3:41])[C@H:36]([C:38](O)=[O:39])[CH3:37])([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>ClCCl.C(OCC)(=O)C>[CH3:2][O:3][C:4](=[O:15])[C:5]1[CH:6]=[CH:7][C:8]([C:11](=[O:14])[CH2:12][NH:13][C:38](=[O:39])[C@@H:36]([N:35]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH3:41])[CH3:37])=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 67046619Methyl 4-(2-aminoacetyl)benzoate hydrochloride

Product 1

HCID 670469924-{2-[2-(S)-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-acetyl}-benzoic acid methyl esterYield 73.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(2-Amino-acetyl)-benzoic acid methyl ester hydrochloride (2.22 mmol), WSC.HCl (2.44 mmol), Boc-N-methyl-(L)-alanine (2.44 mmol) and HOBt (2.77 mmol) were suspended in dichloromethane (10 ml). NMM (2.44 mmol) was added and the reaction stirred for 2 h. The reaction was diluted with ethyl acetate (50 ml) and washed with 10% citric acid (2×25 ml) and saturated sodium hydrogen carbonate (2×25 ml). The organic layer was dried (MgSO4) and the solvent removed in vacuo to give a brown oil residue. Purification by silica chromatography eluting with 10-50% ethyl acetate/iso-hexane gave the title compound (620 mg) as a pale yellow oil m/z=379 in MS ES+.

Workup

  1. washwashed with 10% citric acid (2×25 ml) and saturated sodium hydrogen carbonate (2×25 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customto give a brown oil residue
  5. customPurification by silica chromatography
  6. washeluting with 10-50% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-3fc96cd0b2cc41f7b408ba279598aaca
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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