4-Methylmorpholine → HCID 15291044, compound

HRID 850221Notes

Reaction equation

[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].[NH2:19][C@H:20]([C:24]([N:26]([CH3:42])[C@H:27]([C:31]([N:33]1[CH2:41][CH2:40][CH2:39][C@H:34]1[C:35]([O:37][CH3:38])=[O:36])=[O:32])[CH:28]([CH3:30])[CH3:29])=[O:25])[CH:21]([CH3:23])[CH3:22].CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>ClCCl>[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C@H:2]([C:6]([NH:19][C@H:20]([C:24]([N:26]([CH3:42])[C@H:27]([C:31]([N:33]1[CH2:41][CH2:40][CH2:39][C@H:34]1[C:35]([O:37][CH3:38])=[O:36])=[O:32])[CH:28]([CH3:30])[CH3:29])=[O:25])[CH:21]([CH3:22])[CH3:23])=[O:8])[CH:3]([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 0 °C

Procedure

15.29 g (61 mmol) of Z-Val-OH and 21.96 g (61 mmol) of H-Val-MeVal-Pro-OMe were dissolved in 610 ml of dichloromethane and cooled to 0° C. After addition of 8.16 mol(73.2 mmol) of N-methylmorpholine, 2.77 g (20.3 mmol) of HOBt and 11.74 g (61 mmol) of EDCI, the reaction mixture was stirred overnight at room temperature, diluted with dichloromethane and thoroughly washed with saturated aqueous NaHCO3 solution (3×), water (1×), 5% citric acid (3×) and saturated NaCl solution. The organic phase was dried over sodium sulfate, filtered and evaporated to dryness to yield 31.96 g of the product.

Workup

washthoroughly washed with saturated aqueous NaHCO3 solution (3×), water (1×), 5% citric acid (3×) and saturated NaCl solution
dry with materialThe organic phase was dried over sodium sulfate
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-cdcbac17323044708fd61f8af42c1ae9
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06015790

Reaction notes

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