Trifluoroacetic acid → Fmoc-Phe-Gly-NH(CH2)6-NH2.TFA

HRID 55768Notes

Reaction equation

HRID 55768 reaction equation
[NH:1]([C:31]([O:33][CH2:34][CH:35]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:41]2[C:36]1=[CH:37][CH:38]=[CH:39][CH:40]=2)=[O:32])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23]C(OC(C)(C)C)=O)=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51]>C(Cl)Cl>[NH:1]([C:31]([O:33][CH2:34][CH:35]1[C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:42]2[C:47]1=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:32])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[F:48][C:49]([C:50]([OH:52])=[O:51])([F:54])[F:53]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131733680Fmoc-Phe-Gly-NH-(CH2)6NH-Boc

Product 1

HCID 131733681Fmoc-Phe-Gly-NH(CH2)6-NH2.TFA

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Fmoc-Phe-Gly-NH—(CH2)6NH-Boc (0.7 g) was dissolved in CH2Cl2 (4 mL) at 0° C. under N2 and then trifluoroacetic acid (TFA) (4 mL) was added. The reaction mixture was allowed to warm to RT and stirred for 2 hours under N2. The solvents were removed under reduced pressure and the residue dried at high vacuum to provide 0.71 g of Fmoc-Phe-Gly-NH(CH2)6—NH2.TFA. This crude material was used to prepare without further purification.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue dried at high vacuum

Sources & evidence

ORD record
ord-85e5eb69c63e44fdb5df25b3286fad01
Source dataset
uspto-grants-2016_09
Patent number
US09433600B2

Reaction notes

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