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

HRID 2245215Notes

Reaction equation

HRID 2245215 reaction equation
Cl.[NH2:2][C@@H:3]([C:19]([N:21]1[CH2:35][CH2:34][CH2:33][C@@H:22]1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[C:36](OC(=O)C)(=[O:38])[CH3:37].[OH-].[Na+]>O>[NH:2]([C:36]([CH3:37])=[O:38])[C@@H:3]([C:19]([N:21]1[CH2:35][CH2:34][CH2:33][C@@H:22]1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 131727989H-D-Lys(Z)-D-Pro-OBzl

Product 1

HCID 131727988Ac-D-Lys(Z)-D-Pro-OBzl

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The previously obtained chloromethylene solution of HCl, H-D-Lys(Z)-D-Pro-OBzl is cooled down to 5° C., added with 135 ml of water, followed by 32.3 ml of acetic anhydride (1.5 eq). At Qsp pH 10 is then added within 30 minutes to 1 hour an aqueous 5N NaOH (90 to 130 ml are required).

Sources & evidence

ORD record
ord-1ed88d2884a14607875fe1095dbff306
Source dataset
uspto-grants-2010_03
Patent number
US07683026B2

Reaction notes

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