Ethyl Acetate → HCID 131710170, compound

HRID 1606830Notes

Reaction equation

HRID 1606830 reaction equation
[NH2:1][C@H:2]([C:12]([NH:14][C@H:15]([C:24]([NH:26][C@H:27]([C:37]([NH:39][C@H:40]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:41][O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:38])[CH2:28][CH2:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:25])[CH2:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[C:54]([O:57][CH2:58][CH3:59])(=[O:56])C>>[NH:1]([C:54]([O:57][CH2:58][C:59]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:37]=1)=[O:56])[C@H:2]([C:12]([NH:1][C@H:2]([C:12]([NH:14][C@H:15]([C:24]([NH:26][C@H:27]([C:37]([NH:39][C@H:40]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:41][O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:38])[CH2:28][CH2:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:25])[CH2:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])[CH3:3]

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 131710168HCID 131710168, compound

Product 1

HCID 131710170HCID 131710170, compoundYield 80.7%

Procedure

6.62 g. (8.7 mmoles) of H-28-31-OtBu are dissolved in 65 ml. of ethyl acetate, and 2.72 g. (8.5 mmoles) of Z-Ala-ONSu are added to the solution. After 5 minutes of stirring, a homogeneous solution is formed. The reaction mixture is stirred for one hour; at that time the product separates from the mixture. The mixture is left to stand overnight, thereafter the product is filtered off and washed with ethyl acetate. The crude product is recrystallized from 65 ml. of ethyl acetate. 6.61 g. (80.7 %) of Z-27-31-OtBu are obtained. M.p.: 193°-195° C, Rf11 = 0.75.

Workup

  1. customa homogeneous solution is formed
  2. stirringThe reaction mixture is stirred for one hour
  3. waitThe mixture is left
  4. waitto stand overnight
  5. filtrationthe product is filtered off
  6. washwashed with ethyl acetate
  7. customThe crude product is recrystallized from 65 ml

Sources & evidence

ORD record
ord-8b5d4b52b00a4b749bb23ad9ea6c6248
Source dataset
uspto-grants-1976_04
Patent number
US03953415

Reaction notes

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