Hydrochloric Acid → Ac-D-Lys(Z)-D-Pro-OH

HRID 2245216Notes

Reaction equation

HRID 2245216 reaction equation
[NH:1]([C:35]([CH3:37])=[O:36])[C@@H:2]([C:18]([N:20]1[CH2:34][CH2:33][CH2:32][C@@H:21]1[C:22]([O:24]CC1C=CC=CC=1)=[O:23])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[OH-].[Na+].C(OC(C)C)(C)C.Cl>ClCCl.CO>[NH:1]([C:35]([CH3:37])=[O:36])[C@@H:2]([C:18]([N:20]1[CH2:34][CH2:33][CH2:32][C@@H:21]1[C:22]([OH:24])=[O:23])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 14798Sodium HydroxideHCID 131727988Ac-D-Lys(Z)-D-Pro-OBzl

Product 1

HCID 131727990Ac-D-Lys(Z)-D-Pro-OHYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The Ac-D-Lys(Z)-D-Pro-OBzl compound obtained at the previous steps (in theory: 230 mmol) is mixed with 313 ml of methanol, added with 313 ml of 1N NaOH (313 mmol, 1.36 eq), and stirred overnight at room temperature. The reaction completion is CCM controlled. Thereafter, diisopropyl ether is added (313 ml, 11 vol.), the medium is decanted and the aqueous phase is extracted again three times with 3×150 ml of diisopropyl ether. The aqueous phase is then poured onto a blend of 540 ml of dichloromethane and 70 ml of aqueous 4N HCl (1.2 eq). The blend is stirred for 15 minutes and decanted. The separated organic phase is washed with water followed by a NaCl saturated aqueous solution (110 ml, 4 vol. each time). The organic phase is dried on Na2SO4 and vacuum concentrated (40° C. max, 50 mbar max.). The thus obtained product 94.25 g has the form of a foam (yield=98% calculated based on the involved Boc-D-Lys(Z)-OH).

Workup

  1. customthe medium is decanted
  2. extractionthe aqueous phase is extracted again three times with 3×150 ml of diisopropyl ether
  3. stirringThe blend is stirred for 15 minutes
  4. customdecanted
  5. washThe separated organic phase is washed with water
  6. customThe organic phase is dried on Na2SO4 and vacuum
  7. concentrationconcentrated (40° C. max, 50 mbar max.)

Sources & evidence

ORD record
ord-e4bf9d60684b49e582cdbdba7f24662f
Source dataset
uspto-grants-2010_03
Patent number
US07683026B2

Reaction notes

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