Hydrogen chloride-ethyl acetate → HCID 70044618, compound

HRID 280929Notes

Reaction equation

HRID 280929 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@@H:16]1[C:22](=[O:23])[N:21]([N:24]([C:40](=[O:42])[CH3:41])[C@H:25]([C:33]([O:35]C(C)(C)C)=[O:34])[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:20]2[CH:43]=[CH:44][CH:45]=[CH:46][C:19]=2[O:18][CH2:17]1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].C(OCC)(=O)C.[ClH:53]>>[ClH:53].[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@@H:16]1[C:22](=[O:23])[N:21]([N:24]([C:40](=[O:42])[CH3:41])[C@H:25]([C:33]([OH:35])=[O:34])[CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:20]2[CH:43]=[CH:44][CH:45]=[CH:46][C:19]=2[O:18][CH2:17]1)[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 70044996HCID 70044996, compound

Product 1

HCID 70044618HCID 70044618, compound

Procedure

In 100 ml of hydrogen chloride-ethyl acetate (5N) solution is dissolved 0.4 g of tert-butyl 3(S)-[1(S)-ethoxycarbonyl-3-phenylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-yl-N-acetyl-L-phenylalaninate obtained in Example 24 and the solution is allowed to stand for 4 hours. The reaction solution is concentrated under reduced pressure, and 50 ml of ether is added to the residue. The resulting mixture is extracted twice with 70 ml each of saturated sodium bicarbonate solution and the aqueous layer is extracted with 50 ml of ether. The aqueous layer is neutralized with 1N hydrochloric acid and extracted with 100 ml of ethyl acetate. The ethyl acetate layer is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The oily product is dissolved in 10 ml of ether, and 0.5 ml of hydrogen chloride-ethyl acetate (5N) solution is added to the solution to give 0.2 g of 3(S)-[1(S)-ethoxycarbonyl-3-phenylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-yl-N-acetyl-L-phenylalanine hydrochloride as a colorless powder.

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure, and 50 ml of ether
  2. additionis added to the residue
  3. extractionThe resulting mixture is extracted twice with 70 ml each of saturated sodium bicarbonate solution
  4. extractionthe aqueous layer is extracted with 50 ml of ether
  5. extractionextracted with 100 ml of ethyl acetate
  6. dry with materialThe ethyl acetate layer is dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe oily product is dissolved in 10 ml of ether
  9. addition0.5 ml of hydrogen chloride-ethyl acetate (5N) solution is added to the solution

Sources & evidence

ORD record
ord-b7ab3bb52b154d1a8f717879f9575083
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

Loading…