Hydrochloric Acid → HCID 9825536, compound

HRID 369196Notes

Reaction equation

HRID 369196 reaction equation
[NH2:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.Cl.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C([S:47][CH2:48][CH:49]([CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[C:56]([Br:60])[CH:55]=1)[C:50](O)=[O:51])(=O)C>C(Cl)Cl.C(N(CC)CC)C>[Br:60][C:56]1[CH:55]=[C:54]([CH2:53][CH:49]([CH2:48][SH:47])[C:50]([NH:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)=[O:51])[CH:59]=[CH:58][CH:57]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6305L-TryptophanHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10881645HCID 10881645, compound

Product 1

HCID 9825536HCID 9825536, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

1.88 g of L-Tryptophan in the form of the hydrochloride is introduced into 25 ml of anhydrous methylene chloride and 2.14 ml of triethylamine, 3.1 g of BOP then 2.217 g of the product obtained in Stage 4 above, dissolved in 25 ml of anhydrous methylene chloride, are added. The solution is agitated for 2 hours at ambient temperature, then the solvent is evaporated off, the product obtained in the form of a yellow oil, is then purified by chromatography on silica, with chloroform-ethyl acetate: 85-15 as eluant. After evaporation of the solvent and washing, a yellow gum is obtained. In this way 2.69 g of expected product is obtained (mixture of two diastereoisomers).

Workup

  1. additionare added
  2. customthe solvent is evaporated off
  3. customthe product obtained in the form of a yellow oil
  4. customis then purified by chromatography on silica, with chloroform-ethyl acetate
  5. customAfter evaporation of the solvent
  6. washwashing
  7. customa yellow gum is obtained

Sources & evidence

ORD record
ord-23af68c5b51647f29c68dada01174c67
Source dataset
uspto-grants-2000_10
Patent number
US06136842

Reaction notes

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