4-Methylmorpholine → HCID 18642403, compound

HRID 1111310Notes

Reaction equation

HRID 1111310 reaction equation
[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[C:37]([NH:44][C:45]([O:47][CH:48]([CH3:50])[CH3:49])=[O:46])[CH:36]=1>O1CCCC1>[C:45]([NH:44][C:37]1[CH:36]=[C:35]([NH:34][C:13](=[O:15])[C@@H:12]2[CH2:16][CH2:17][CH2:18][N:11]2[C:1]([O:3][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2])[CH:43]=[CH:42][C:38]=1[C:39]([OH:41])=[O:40])([O:47][CH:48]([CH3:50])[CH3:49])=[O:46]

Participants

6

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 101987Benzyloxycarbonyl-L-prolineHCID 22152159HCID 22152159, compound

Product 1

HCID 18642403HCID 18642403, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

A solution was prepared by dissolving 249 mg of N-carbobenzoxy-L-proline and 101.0 mg of N-methylmorpholine in 5 ml of dry tetrahydrofuran and cooling to a temperature of -15° C. The solution was mixed with 136.6 mg of isobutyl chloroformate and the mixture was stirred at a temperature of -15° C. to -10° C. for 2 minutes. Then, a solution of 238 mg of 4-amino-2-carboisopropoxyaminobenzoic acid and 101.2 mg of N-methylmorpholine in 2 ml of dry tetrahydrofuran was added dropwise to the above-mentioned mixture. The resultant reaction mixture was stirred at a temperature of -15° C. to -10° C. for one hour, gradually heated to room temperature, and then stirred at room temperature for 18 hours. The resultant deposit generated in the reaction mixture was removed by filtration, the filtrate was concentrated under a reduced pressure, and an oily yellow substance was obtained.

Workup

  1. customA solution was prepared
  2. customThe resultant reaction mixture
  3. stirringwas stirred at a temperature of -15° C. to -10° C. for one hour
  4. temperaturegradually heated to room temperature
  5. stirringstirred at room temperature for 18 hours
  6. customwas removed by filtration
  7. concentrationthe filtrate was concentrated under a reduced pressure
  8. customan oily yellow substance was obtained

Sources & evidence

ORD record
ord-a7054b498dba4f389f580038aa0fa1ed
Source dataset
uspto-grants-1990_12
Patent number
US04980287

Reaction notes

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