Acetic Acid → 3-({4-[(4-Tert-butylcyclohexylamino)methyl]benzoyl}cyclopropylmethylamino)propionic acid

HRID 1633890Notes

Reaction equation

[CH:1]1([CH2:4][N:5]([C:11](=[O:20])[C:12]2[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=2)[CH2:6][CH2:7][C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1.[C:21]([CH:25]1[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27][CH2:26]1)([CH3:24])([CH3:23])[CH3:22].C(O)(=O)C.C([BH3-])#N.[Na+]>CN(C=O)C.COC(OC)OC>[C:21]([CH:25]1[CH2:26][CH2:27][CH:28]([NH:31][CH2:18][C:15]2[CH:16]=[CH:17][C:12]([C:11]([N:5]([CH2:4][CH:1]3[CH2:3][CH2:2]3)[CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:20])=[CH:13][CH:14]=2)[CH2:29][CH2:30]1)([CH3:24])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 25 °C

Procedure

The above resin bound 3-[cyclopropylmethyl-(4-formylbenzoyl)amino]propionic acid (50 mg) was treated with 1 mL 0.5 M (0.5 mmol, 77.5 mg) 4-tert-butylcyclohexylamine solution in DMF:trimethylorthoformate 1:1, 100 μL glacial acetic acid and sodium cyanoborohydride (750 μmol, 48 mg) suspended in 0.5 mL DMF:trimethylorthoformate 1:1. Overnight shaking at 25° C. followed by filtration and washing with 2×1 mL 20% H2O in DMF, 3×1 mL DMF and 2×1 mL dichloromethane afforded the desired product.

Workup

filtrationfollowed by filtration
washwashing with 2×1 mL 20% H2O in DMF, 3×1 mL DMF and 2×1 mL dichloromethane

Sources & evidence

ORD record: ord-90fd8fd37fb546b4b8009babf5834053
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503949B1

Reaction notes

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