Pyridine → HCID 131711822, compound

HRID 2057853Notes

Reaction equation

HRID 2057853 reaction equation
[NH:1](C(OC(C1C=C(OC)C=C(OC)C=1)(C)C)=O)[C@H:2]([C:24]([NH:26][C@H:27]([C:35]([NH:37][C@H:38]([C:45]([OH:47])=[O:46])[CH2:39][O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:36])[C@@H:28]([CH3:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:25])[CH2:3][S:4][C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N1C=CC=CC=1.[F:70][C:71]([F:76])([F:75])[C:72]([OH:74])=[O:73]>O.C(Cl)Cl>[NH2:1][C@H:2]([C:24]([NH:26][C@H:27]([C:35]([NH:37][C@H:38]([C:45]([OH:47])=[O:46])[CH2:39][O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:36])[C@@H:28]([CH3:34])[O:29][C:30]([CH3:33])([CH3:31])[CH3:32])=[O:25])[CH2:3][S:4][C:5]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F:70][C:71]([C:72]([OH:74])=[O:73])([F:76])[F:75]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6422Trifluoroacetic acid2×HCID 131711824HCID 131711824, compound

Product 1

HCID 131711822HCID 131711822, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

8.8 g (10 mmoles) of Ddz-Cys(Trt)-Thr(But)-Ser(But)-OH are dissolved at room temperature in a mixture of 8.75 ml (0.1 mole) of trifluoroacetic acid, 1.75 ml of water and 165 ml of methylene chloride (=about 175 ml of a 5% strength solution of trifluoroacetic acid in methylene chloride, containing 1% of water). The mixture is left to stand at room temperature for 1.5 hours and is then neutralized with 8.85 ml (0.11 mole) of pyridine. The solution is concentrated and the residue is partitioned between ethyl acetate and water. The ethyl acetate phase is washed twice more with water and is dried over Na2SO4 and concentrated. The residue is dissolved in a small amount of ether and the solution is slowly added dropwise to petroleum ether.

Workup

  1. waitThe mixture is left
  2. concentrationThe solution is concentrated
  3. customthe residue is partitioned between ethyl acetate and water
  4. washThe ethyl acetate phase is washed twice more with water
  5. dry with materialis dried over Na2SO4
  6. concentrationconcentrated
  7. dissolutionThe residue is dissolved in a small amount of ether
  8. additionthe solution is slowly added dropwise to petroleum ether

Sources & evidence

ORD record
ord-2765c2c726ac4f8faef28bbdf40ed2a9
Source dataset
uspto-grants-1980_07
Patent number
US04212796

Reaction notes

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