HCID 131711922, compound → HCID 131711921, compound

HRID 904042Notes

Reaction equation

HRID 904042 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:12]([NH:14][C@H:15]([C:28]([NH:30][C@H:31]([C:34]([NH:36][C@H:37]([C:43]([NH:45][CH2:46][C:47]([NH:49][C@@H:50]([C:52]([NH:54][C@H:55]([C:58]([NH:60][C@H:61]([C:66]([O:68]C(C)(C)C)=[O:67])[CH2:62][C:63](=[O:65])[NH2:64])=[O:59])[CH2:56][OH:57])=[O:53])[CH3:51])=[O:48])=[O:44])[CH2:38][CH2:39][C:40](=[O:42])[NH2:41])=[O:35])[CH2:32][OH:33])=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20]C(OC(C)(C)C)=O)=[O:13])[CH3:11])=[O:8]>FC(F)(F)C(O)=O>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:12]([NH:14][C@H:15]([C:28]([NH:30][C@H:31]([C:34]([NH:36][C@H:37]([C:43]([NH:45][CH2:46][C:47]([NH:49][C@@H:50]([C:52]([NH:54][C@H:55]([C:58]([NH:60][C@H:61]([C:66]([OH:68])=[O:67])[CH2:62][C:63](=[O:65])[NH2:64])=[O:59])[CH2:56][OH:57])=[O:53])[CH3:51])=[O:48])=[O:44])[CH2:38][CH2:39][C:40](=[O:42])[NH2:41])=[O:35])[CH2:32][OH:33])=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])=[O:13])[CH3:11])=[O:8]

Participants

3

Reactant 1

HCID 131711922HCID 131711922, compound

Product 1

HCID 131711921HCID 131711921, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

In 5 ml of trifluoroacetic acid is dissolved 500 mg of pGlu-Ala-Lys(Boc)-Ser-Gln-Gly-(D)-Ala-Ser-Asn-OBut and the mixture is allowed to stand at room temperature. The trifluoroacetic acid is distilled off and the residue is precipitated with ether and recovered by filtration. The resulting powders are dissolved in 50 ml of water and run onto a column of Amberlite IRA-410(acetate-form) (2×5 cm). The effluent is combined with washings and lyophilized. The powdery lyophilizate is dissolved in a small amount of 0.1 N-aqueous acetic acid and put onto a column of Sephadex LH-20 (2.5×125 cm), elution being carried out with 0.1 N-aqueous acetic acid. The fractions from 186 ml through 206 ml are pooled and lyophilized. Yield 310 mg (62%); [α]D24 -47.3°(c=0.35, H2O); Rf4 (Avicel)=0.24; amino acid analysis (acid hydrolyzate); Lys, 1.08(1); Asp, 1.00(1); Ser, 1.90(2); Glu, 1.93(2); Gly, 1.06(1); Ala, 2.00(2); average recovery 89%.

Workup

  1. customto stand at room temperature
  2. distillationThe trifluoroacetic acid is distilled off
  3. customthe residue is precipitated with ether
  4. filtrationrecovered by filtration
  5. dissolutionThe resulting powders are dissolved in 50 ml of water
  6. dissolutionThe powdery lyophilizate is dissolved in a small amount of 0.1 N-aqueous acetic acid
  7. wash(2.5×125 cm), elution

Sources & evidence

ORD record
ord-311a272c595e4bbd90061007ffb60838
Source dataset
uspto-grants-1980_10
Patent number
US04229438

Reaction notes

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