Hydrochloric Acid → H-Phe-(D)Trp-Lys(Z)-Thr-Cys(MBzl)-Thr-ol hydrochloride

HRID 1903343Notes

Reaction equation

HRID 1903343 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:10]([NH:12][C@@H:13]([C:24]([NH:26][C@H:27]([C:43]([NH:45][C@H:46]([C:50]([NH:52][C@H:53]([C:64]([NH:66][C@H:67]([CH2:71][OH:72])[C@@H:68]([CH3:70])[OH:69])=[O:65])[CH2:54][S:55][CH2:56][C:57]1[CH:63]=[CH:62][C:60]([CH3:61])=[CH:59][CH:58]=1)=[O:51])[C@@H:47]([CH3:49])[OH:48])=[O:44])[CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])=[O:25])[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[ClH:80]>C(O)(C(F)(F)F)=O.O.C(OCC)C>[NH2:1][C@H:2]([C:10]([NH:12][C@@H:13]([C:24]([NH:26][C@H:27]([C:43]([NH:45][C@H:46]([C:50]([NH:52][C@H:53]([C:64]([NH:66][C@H:67]([CH2:71][OH:72])[C@@H:68]([CH3:70])[OH:69])=[O:65])[CH2:54][S:55][CH2:56][C:57]1[CH:63]=[CH:62][C:60]([CH3:61])=[CH:59][CH:58]=1)=[O:51])[C@@H:47]([CH3:49])[OH:48])=[O:44])[CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:34])=[O:25])[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[ClH:80]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131713420BOC-Phe-(D)Trp-Lys(Z)-Thr-Cys(MBzl)-Thr-ol

Product 1

HCID 131713421H-Phe-(D)Trp-Lys(Z)-Thr-Cys(MBzl)-Thr-ol hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

13 g BOC-Phe-(D)Trp-Lys(Z)-Thr-Cys(MBzl)-Thr-ol are dissolved in 60 ml cold TFA/H2O (15:1) and the solution allowed to stand for 30 min. at room temperature. The reaction mixture is stirred into a mixture comprising 3 liters ethyl-ether and 20 ml HCl in ethyl-ether (~5 N) and the precipitated product filtered off, washed with ethyl-ether and dried to yield the title compound:

Workup

  1. filtrationthe precipitated product filtered off
  2. washwashed with ethyl-ether
  3. customdried

Sources & evidence

ORD record
ord-37b3c6a1be8748ec9f8dd6ccf5c2e844
Source dataset
uspto-grants-1984_03
Patent number
US04435385

Reaction notes

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