Tetrahydrofuran → HCID 14837130, compound

HRID 1031757Notes

Reaction equation

HRID 1031757 reaction equation
C(OC(NC[C@H]1CC[C@H:13]([C:16]([NH:18][C:19](=[O:29])[C@H:20]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[NH2:21])=O)CC1)=O)(C)(C)C.C(N(CC)CC)C.[Cl:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].[O:43]1CCCC1>>[ClH:37].[NH2:21][C@H:20]([C:19]([NH:18][C@H:16]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:13][OH:43])=[O:29])[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178453621HCID 178453621, compound

Product 1

HCID 14837130HCID 14837130, compound

Procedure

N-(t-butoxycarbonyl)-3-phenoxy-DL-phenylalanine (I) (7.42 g) obtained in (4) was dissolved in dry tetrahydrofuran (80 ml), triethylamine (3 ml) was added to the solution, and further, ethyl chloroformate (2.40 g) was added under ice-cooling, followed by stirring for 30 minutes. To the solution, 4-acetylanilide (2.70 g) was added and the mixture was stirred under room temperature for 10 hours. To the reaction mixture, ice-water (300 ml) was added, and the crystalline substance precipitated was collected by filtration, thoroughly washed with water, and then dried to obtain N-(t-butoxycarbonyl)-3-phenoxy-DL-phenylalanine 4-acetylanilide (II) 7.07 g) as a white powder. The structure was confirmed by IR and NMR.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred under room temperature for 10 hours
  3. customthe crystalline substance precipitated
  4. filtrationwas collected by filtration
  5. washthoroughly washed with water
  6. customdried

Sources & evidence

ORD record
ord-160554e3b4904b3984e330fdd62be408
Source dataset
uspto-grants-1990_09
Patent number
US04954512

Reaction notes

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