4-Methylmorpholine → HCID 56637722, compound

HRID 1532908Notes

Reaction equation

[O:1]=[C:2]1[NH:8][C:7]2[C:9]([CH3:14])=[CH:10][C:11]([CH3:13])=[CH:12][C:6]=2[NH:5][CH2:4][C@@H:3]1[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(OC(N[C@@H](CN[C:37]1[CH:42]=[C:41](C)[CH:40]=[C:39]([CH3:44])[C:38]=1N)C(O)=O)=O)(C)(C)C.CN1[CH2:52][CH2:51][O:50]CC1.C([O:57]C(Cl)=O)C(C)C>C1COCC1.CCOC(C)=O>[CH2:44]([O:50][C:51](=[O:57])[CH2:52][N:8]1[C:7]2[C:9]([CH3:14])=[CH:10][C:11]([CH3:13])=[CH:12][C:6]=2[NH:5][CH2:4][C@H:3]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:2]1=[O:1])[C:39]1[CH:38]=[CH:37][CH:42]=[CH:41][CH:40]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-Oxo-(3S)-3-tert-butoxycarbonylamino-2,3,4,5-tetrahydro-7,9-dimethyl-1H-1,5-benzodiazepine. A 0° C. solution of (2S)-2-tert-butoxycarbonylamino-3-(2-amino-3,5-dimethylphenyl-amino)-propionic acid (763 mg, 2.36 mmol) and N-methylmorpholine (483 mg, 4.78 mmol) in 60 ml of anhydrous THF was treated dropwise with isobutylchloroformate (352 mg, 2.5 mmol). The reaction was stirred for 2 h at 0° C., at RT for 1 h and poured over EtOAc. The mixture was washed with aq. 5% NaHSO4, sat. aq. NaHCO3, and sat. aq. NaCl, dried over NaSO4, and concentrated in vacuo. Chromatography (flash, SiO2, 10% to 25% to 50% EtOAc/CH2Cl2) gave 490 mg (68%) of the desired product.

Workup

washThe mixture was washed with aq. 5% NaHSO4, sat. aq. NaHCO3, and sat. aq. NaCl
dry with materialdried over NaSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-dd657fd97a0f4d3da66b3deae33e629e
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06204261B1

Reaction notes

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