Aniline → HCID 35369893, compound

HRID 1448728Notes

Reaction equation

HRID 1448728 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([OH:20])=O)=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCOCC1)C.ClC(OCC(C)C)=O.[NH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>O1CCCC1.CCOCC>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([NH:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:20])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 7525Ethylmorpholine2×HCID 62365Isobutyl chloroformateHCID 5388928Z-Ala Prolinal

Product 1

HCID 35369893HCID 35369893, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

32 g (0.1 mol) of N-benzyloxycarbonyl-L-alanyl-L-proline were dissolved in 300 ml of dry tetrahydrofuran and the solution was cooled to -10° C. 12.7 ml (0.1 mol) of N-ethylmorpholine and 13.1 ml (0.1 mol) of isobutyl chloroformate were added and the solution was stirred for 20 minutes while maintaining the temperature at -10° C. 9.3 ml of aniline were then added and the mixture was stirred at 0° C. for 1 hour. The mixture was found to be slightly acidic and a further 1 g of N-ethylmorpholine was added. The solution was then left to stand at room temperature for 16 hours. The solution was evaporated, there being obtained a white crystalline solid which was treated with 500 ml of ether, filtered, washed and dried to give 31.8 g of N-benzyloxycarbonyl-L-alanyl-L-proline anilide of melting point 139.5°-140.5° C.; [α]D20 =-125.5° (c=1.195% in methanol). A second crop (1.4 g; melting point 138°-139° C.) was obtained by evaporating the mother liquor to a small volume, when crystallisation took place. The total yield was 81%.

Workup

  1. temperaturewhile maintaining the temperature at -10° C
  2. stirringthe mixture was stirred at 0° C. for 1 hour
  3. waitThe solution was then left
  4. waitto stand at room temperature for 16 hours
  5. customThe solution was evaporated
  6. customthere being obtained a white crystalline solid which
  7. filtrationfiltered
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-b3959c173e764fe59ca384df00557763
Source dataset
uspto-grants-1980_02
Patent number
US04187216

Reaction notes

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