Trifluoroacetic acid → HCID 131711394, compound

HRID 2163180Notes

Reaction equation

HRID 2163180 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:6]([N:8]1[CH2:46][CH2:45][CH2:44][C@H:9]1[C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:28]([NH:30][CH2:31][C:32]([O:34][C:35]1[CH:43]=[CH:42][C:38]([N+:39]([O-:41])=[O:40])=[CH:37][CH:36]=1)=[O:33])=[O:29])[CH2:18][CH:19](OC(C)(C)C)[C:20](=[O:22])[OH:21])=[O:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].[F:54][C:55]([F:60])([F:59])[C:56]([OH:58])=[O:57]>C(Cl)Cl>[NH2:1][C@H:2]([C:6]([N:8]1[CH2:46][CH2:45][CH2:44][C@H:9]1[C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:28]([NH:30][CH2:31][C:32]([O:34][C:35]1[CH:36]=[CH:37][C:38]([N+:39]([O-:41])=[O:40])=[CH:42][CH:43]=1)=[O:33])=[O:29])[CH2:18][CH2:19][C:20](=[O:21])[OH:22])=[O:15])=[O:11])=[O:7])[CH:3]([CH3:4])[CH3:5].[F:54][C:55]([C:56]([OH:58])=[O:57])([F:60])[F:59]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131711393HCID 131711393, compound

Product 1

HCID 131711394HCID 131711394, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of XX (1.1 g, 1.50 mmol) in 9 ml of 30% trifluoroacetic acid in methylene chloride was allowed to stand for 30 min. at room temperature. The reaction mixture was treated in the same manner as described for the preparation of XI in part (j). The resulting solid was recrystallized from chloroform-petroleum ether; yield 0.923 g (90%), m.p. 130-133° C., Rf1 0.06, Rf2 0.12, Rf3 0.21. Calcd. for C27H35N6O12F3.1/2H2O: C, 46.22; H, 5.17; N, 11.98%. Found: C, 46.06; H, 5.16; N, 11.82%. Amino acid analysis: Glu, 0.98; Pro, 0.90; Gly, 2.10; Val, 1.00.

Workup

  1. additionThe reaction mixture was treated in the same manner
  2. customThe resulting solid was recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-2bbb4517849e46ecb5b78aa9e842edac
Source dataset
uspto-grants-1979_01
Patent number
US04132746

Reaction notes

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