4-Methylmorpholine → HCID 131721607, compound

HRID 1871667Notes

Reaction equation

HRID 1871667 reaction equation
[NH:1]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C@H:2]([C:6]([NH:8][C@H:9]([C:13]([N:15]([CH3:30])[C@H:16]([C:20](N1CCC[C@H]1C(O)=O)=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])[CH:3]([CH3:5])[CH3:4].[NH:41]1[CH2:51][CH2:50][CH2:49][C@H:42]1[C:43]([NH:45][CH:46]([CH3:48])[CH3:47])=[O:44].CN1CC[O:56]CC1.C1C=C[C:62]2N(O)N=[N:65][C:63]=2[CH:64]=1.CCN=C=NC[CH2:75][CH2:76]N(C)C>ClCCl>[NH:1]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C@H:2]([C:6]([NH:8][C@H:9]([C:13]([N:15]([CH3:30])[C@H:16]([C:20]([N:41]1[CH2:51][CH2:50][CH2:49][C@H:42]1[C:43]([N:45]1[CH2:76][CH2:75][CH2:48][C@H:46]1[C:47]([NH:65][CH:63]([CH3:64])[CH3:62])=[O:56])=[O:44])=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14])[CH:10]([CH3:11])[CH3:12])=[O:7])[CH:3]([CH3:4])[CH3:5]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 10507094HCID 10507094, compoundHCID 10898944HCID 10898944, compound

Product 1

HCID 131721607HCID 131721607, compoundYield 333.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2 g (3.35 mmol) Z-Val-Val-MeVal-Pro-OH and 0.664 g (3.35 mmol) H-Pro-NHCH(CH3)2 were dissolved in 34 ml of dry dichloromethane. After cooling to 0° C., 1.35 ml (12.1 mmol) N-methylmorpholine, 0.114 g (0.84 mmol) HOBt and 0.645 g (3.35 mmol) EDCI were added and the reaction mixture stirred overnight at room temperature. 80 ml dichloromethane were added and the organic phase thoroughly washed with saturated aqueous NaHCO3 solution (3×), water (1×), 5% citric acid (3×) and saturated NaCl solution (1×). The organic phase was dried over sodium sulfate, filtered and evaporated to dryness to yield 1.96 g of the product which was used in the next reaction without further purification.

Workup

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

Sources & evidence

ORD record
ord-ce32027526ad41ff885e5de71cc9da04
Source dataset
uspto-grants-2000_08
Patent number
US06103698

Reaction notes

Loading…