Hydrogen Bromide → HCID 178512869, compound

HRID 1461976Notes

Reaction equation

HRID 1461976 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:10]([N:12]1[CH2:41][CH2:40][CH2:39][C@H:13]1[C:14]([NH:16][C@H:17]([C:25]([NH:27][C@H:28]([C:36]([OH:38])=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:26])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:24])[NH2:23])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[NH2:1][C@@H:2]([C:10]([N:12]1[CH2:41][CH2:40][CH2:39][C@H:13]1[C:14]([NH:16][C@H:17]([C:25]([NH:27][C@H:28]([C:36]([OH:38])=[O:37])[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:26])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:23])[NH2:24])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 178454149HCID 178454149, compound

Product 1

HCID 178512869HCID 178512869, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

450 mg (0.44 mmole) of Boc-D-Phe-Pro-Arg-Phe-pNa.HBr are dissolved in 4 ml of trifluoroacetic acid, with the addition of 0.1 ml of anisole, and the solution is stirred at room temperature for 45 minutes. The product is precipitated with ether, centrifuged off and triturated with ether and centrifuged off again several times. The dried substance is triturated with NaHCO3 solution, the mixture is extracted with n-butanol, the organic phase is dried with K2CO3 and filtered and the filtrate is evaporated to dryness. The solid residue is triturated with ether and centrifuged off.

Workup

  1. customThe product is precipitated with ether
  2. customtriturated with ether
  3. customThe dried substance is triturated with NaHCO3 solution
  4. extractionthe mixture is extracted with n-butanol
  5. dry with materialthe organic phase is dried with K2CO3
  6. filtrationfiltered
  7. customthe filtrate is evaporated to dryness
  8. customThe solid residue is triturated with ether

Sources & evidence

ORD record
ord-23c8458ab22d4e1fb5ddcf905db396e7
Source dataset
uspto-grants-1984_07
Patent number
US04457866

Reaction notes

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