Acetate → HCID 131711925, compound

HRID 904044Notes

Reaction equation

HRID 904044 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][C@@H:46]([C:51]([NH:53][CH2:54][C:55]([NH:57][C@H:58]([C:61]([NH:63][C@H:64]([C:69]([O:71]C(C)(C)C)=[O:70])[CH2:65][C:66](=[O:68])[NH2:67])=[O:62])[CH2:59][OH:60])=[O:56])=[O:52])[CH2:47][CH:48]([CH3:50])[CH3:49])=[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].C([O-])(=O)C>FC(F)(F)C(O)=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][C@@H:46]([C:51]([NH:53][CH2:54][C:55]([NH:57][C@H:58]([C:61]([NH:63][C@H:64]([C:69]([OH:71])=[O:70])[CH2:65][C:66](=[O:68])[NH2:67])=[O:62])[CH2:59][OH:60])=[O:56])=[O:52])[CH2:47][CH:48]([CH3:50])[CH3:49])=[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

5

Reactant 2

HCID 175AcetateHCID 131711926HCID 131711926, compound

Product 1

HCID 131711925HCID 131711925, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

In 8 ml of trifluoroacetic acid is dissolved 200 mg of pGlu-Ala-Lys(Boc)-Ser-Gln-(D)-Leu-Gly-Ser-Asn-OBut and the solution is allowed to stand at room temperature for 60 minutes. The trifluoroacetic acid is distilled off under reduced pressure and the residue is precipitated with ether and recovered by filtration. The powders thus obtained are dissolved in a small amount of water and passed through a column of Amberlite IRA-410 (acetate-form) (1.5×7 cm). The effluent is combined with washings and lyophilized. The powdery lyophilizate is dissolved in a small amount of 1 N-acetic acid and put onto a chromatographic column of Sephadex LH-20(2.5×125 cm), elution being carried out with 1 N-acetic acid. The fractions from 190-205 ml are pooled and lyophilized. Yield 65 mg; [α]D22 -45.4° (c=0.4, H2O); Rf4 (Avicel)=0.37; amino acid analysis (acid hydrolyzate): Lys, 1.04(1); Asp, 0.98(1); Ser, 1.86 (2); Glu, 2.14(2); Gly, 0.93(1); Ala, 1.00(1); Leu, 1.00 (1); average recovery, 71.2%.

Workup

  1. distillationThe trifluoroacetic acid is distilled off under reduced pressure
  2. customthe residue is precipitated with ether
  3. filtrationrecovered by filtration
  4. customThe powders thus obtained
  5. wash×125 cm), elution

Sources & evidence

ORD record
ord-fc9ec632ec4841ef9520d8673cf430a4
Source dataset
uspto-grants-1980_10
Patent number
US04229438

Reaction notes

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