Benzyl isocyanate → HCID 131723737, compound

HRID 1634047Notes

Reaction equation

[NH2:1][C:2]1[CH:34]=[CH:33][C:5]2[NH:6][C:7](=[O:32])[C@H:8]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[N:9]([CH2:12][C:13]([NH:15][CH:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][C:18]([OH:20])=[O:19])=[O:14])[C:10](=[O:11])[C:4]=2[CH:3]=1.[CH2:35]([N:42]=[C:43]=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C=O)C>[CH2:35]([NH:42][C:43](=[O:44])[NH:1][C:2]1[CH:34]=[CH:33][C:5]2[NH:6][C:7](=[O:32])[C@H:8]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[N:9]([CH2:12][C:13]([NH:15][CH:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][C:18]([OH:20])=[O:19])=[O:14])[C:10](=[O:11])[C:4]=2[CH:3]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 3-(R,S)-{2-[7-amino-3-(S)-(2-carboxy-ethyl)-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-acetylamino}-3-phenyl-propionic acid (0.15 mmol, 70 mg) in DMF (2.5 ml) was added benzylisocyanate (46 μl, 037 mmol). The mixture was shaken at 45° C. over night. Then the solution was evaporated and the crude product was purified by RP-HPLC to give 3-(R,S)-{2-[7-(3-benzyl-ureido)-3-(S)-(2-carboxy-ethyl)-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-acetylamino}-3-phenyl-propionic acid (14 mg): MS (ISN) 600 (M−H)−.

Workup

customThen the solution was evaporated
customthe crude product was purified by RP-HPLC

Sources & evidence

ORD record: ord-d917cf873ac24578933fe507721cd847
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506744B1

Reaction notes

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