Trifluoroacetic acid → H-(D)Trp-Lys(Z)-OMe hydrochloride

HRID 1903339Notes

Reaction equation

HRID 1903339 reaction equation
C(O)(C(F)(F)F)=O.[NH:8](C(OC(C)(C)C)=O)[C@@H:9]([C:20]([NH:22][C@H:23]([C:39]([O:41][CH3:42])=[O:40])[CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1.[ClH:50].C(OCC)C>C(Cl)Cl.C(OCC)C>[NH2:8][C@@H:9]([C:20]([NH:22][C@H:23]([C:39]([O:41][CH3:42])=[O:40])[CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1.[ClH:50]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10953452Ether hydrochlorideHCID 13391303BOC-(D)Trp-Lys(Z)-OMe

Product 1

HCID 13391306H-(D)Trp-Lys(Z)-OMe hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

150 ml TFA are added to 30 g BOC-(D)Trp-Lys(Z)-OMe in 150 ml methylene chloride pre-cooled to 0° C. The whole is stirred for 40 minutes at room-temperature and then added to 30 ml HCl/ethyl-ether (~5 N) in 4 l ethyl-ether. After thorough stirring the precipitate is filtered off, washed with ethyl-ether and dried to yield the title compound:

Workup

  1. stirringAfter thorough stirring the precipitate
  2. filtrationis filtered off
  3. washwashed with ethyl-ether
  4. customdried

Sources & evidence

ORD record
ord-758c82f3ccaf4e8484c977c337b64009
Source dataset
uspto-grants-1984_03
Patent number
US04435385

Reaction notes

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