4-Nitrophenyl chloroformate → HCID 18957756, compound

HRID 2379363Notes

Reaction equation

[NH2:1][CH:2]1[N:8]=[C:7]([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[N:4]([CH2:18][CH2:19][CH3:20])[C:3]1=[O:21].Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:24]>>[CH:9]1([C:7]2[C:6]3[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=3[N:4]([CH2:18][CH2:19][CH3:20])[C:3](=[O:21])[CH:2]([NH:1][C:23]([O:25][C:26]3[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=3)=[O:24])[N:8]=2)[CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

Reactant 2

HCID 821294-Nitrophenyl chloroformate

HCID 18957791HCID 18957791, compound

Product 1

HCID 18957756HCID 18957756, compoundYield 78%

Procedure

The title compound was prepared from 3(R,S)-amino-5-cyclopentyl-1,3-dihydro-1-propyl-2H-1,4-benzodiazepin-2-one (321 mg, 11.2 mmol) and 4-nitrophenyl chloroformate (229 mg, 11.4 mmol) using the procedure described in Example 20, Step 1. The crude product was triturated with ether (10 ml) to give the title compound (396 mg, 78%) as a white solid. 1H NMR (360 MHz, CDCl3) 0.83 (3H, t, J=7.4 Hz), 1.33-1.82 (8H, m), 1.97 (1H, m), 2.15 (1H, m), 3.34 (1H, m), 3.60 (1H, m), 4.32 (1H, m), 5.16 (1H, d, J=8.3 Hz), 6.89 (1H, d, J=8.4 Hz), 7.30-7.37 (4H, m), 7.52 (1H, t of d, J=7.8 and 1.6 Hz), 7.59 (1H, dd, J=7.8 and 1.5 Hz), 8.22 (2H, d, J=9.2 Hz).

Workup

customThe crude product was triturated with ether (10 ml)

Sources & evidence

ORD record: ord-f61d26fda4604182a023493f76238a80
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05360802

Reaction notes

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