Water → BOC-Phe-(D)Trp-Lys(Z)-OH

HRID 1903341Notes

Reaction equation

HRID 1903341 reaction equation
[OH-].[Na+].[NH:3]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[C@H:4]([C:12]([NH:14][C@@H:15]([C:26]([NH:28][C@H:29]([C:45]([O:47]C)=[O:46])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])=[O:27])[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O>O1CCOCC1.O>[NH:3]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[C@H:4]([C:12]([NH:14][C@@H:15]([C:26]([NH:28][C@H:29]([C:45]([OH:47])=[O:46])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])=[O:27])[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)=[O:13])[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13391308BOC-Phe-(D)Trp-Lys(Z)-OMe

Product 1

HCID 13391310BOC-Phe-(D)Trp-Lys(Z)-OH

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

26 ml 1 N NaOH are added to a suspension of 16 g BOC-Phe-(D)Trp-Lys(Z)-OMe in dioxane/H2O (8:2) and the reaction mixture stirred for 1.5 hrs. at room temperature. The obtained solution is diluted to ca. 500 ml by the addition of H2O and then concentrated under vacuum. The pH is adjusted to 1.5 to 2 by the addition, with stirring, of 1 N HCl, the precipitated product is filtered off, washed with H2O until neutral and dried to yield the title compound:

Workup

  1. customat room temperature
  2. concentrationconcentrated under vacuum
  3. additionThe pH is adjusted to 1.5 to 2 by the addition
  4. stirringwith stirring, of 1 N HCl
  5. filtrationthe precipitated product is filtered off
  6. washwashed with H2O until neutral and
  7. customdried

Sources & evidence

ORD record
ord-6d19a594192e4566b70c8f0c1a78392d
Source dataset
uspto-grants-1984_03
Patent number
US04435385

Reaction notes

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