Acetic Acid → 3-{4-[(4-propylcyclohexylamino)methyl]benzoylamino}propionic Acid

HRID 1633885Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([NH:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:8])=[CH:5][CH:4]=1.[CH2:17]([CH:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1)[CH2:18][CH3:19].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:17]([CH:20]1[CH2:25][CH2:24][CH:23]([NH:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([C:7]([NH:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:8])=[CH:15][CH:16]=2)[CH2:22][CH2:21]1)[CH2:18][CH3:19]

Participants

Conditions

Temperature: 25 °C

Procedure

The resulting resin bound 3-(4-aminomethylbenzoylamino)propionic acid was treated with 98 mg 4-propylcyclohexanone (700 μmol) dissolved in 500 μL 1,2-dichloroethane, 50 μL acetic acid and a slurry of 148 mg NaBH(OAc)3 (700 μmol) in 1 mL 1,2-dichloroethane. Over night shaking at 25° C. followed by filtration and washing with 2×1 mL dichloromethane, 2×1 mL CH3OH:DMF 1:1 and 3×1 mL DMF afforded resin bound 3-{4-[(4-propylcyclohexylamino)-methyl]benzoylamino}propionic acid.

Workup

filtrationfollowed by filtration
washwashing with 2×1 mL dichloromethane, 2×1 mL CH3OH:DMF 1:1 and 3×1 mL DMF afforded resin

Sources & evidence

ORD record: ord-b55b2ab7bddf4ce68af9fc3aeec264c3
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503949B1

Reaction notes

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