Hydrochloric Acid → HCID 15858327, compound

HRID 369200Notes

Reaction equation

HRID 369200 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[C:62]([Cl:63])=[CH:61][C:57]2[O:58][CH2:59][O:60][C:56]=2[CH:55]=1)[C:50](O)=[O:51])(=O)C>C(Cl)Cl.C(N(CC)CC)C>[Cl:63][C:62]1[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:55][C:56]2[O:60][CH2:59][O:58][C:57]=2[CH:61]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6305L-TryptophanHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 23285632HCID 23285632, compound

Product 1

HCID 15858327HCID 15858327, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

The operation is carried out as in Stage 5 of Example 1, starting with 121 mg of L-Tryptophan in the form of the hydrochloride, 2 ml of anhydrous methylene chloride, 0.13 ml of triethylamine, 199 mg of BOP and 143 mg of the product obtained in Stage 5 above, dissolved in 3 ml of anhydrous methylene chloride. Purification is carried out by chromatography on silica with chloroform-ethyl acetate: 90-10 as eluant. In this way 133 mg of expected product (yellow gum) is obtained.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-7bfb45f9f6b1410b87c93c1d7406f4da
Source dataset
uspto-grants-2000_10
Patent number
US06136842

Reaction notes

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