Chloroform methanol → HCID 14135690, compound

HRID 373296Notes

Reaction equation

HRID 373296 reaction equation
[NH:1]([C:14]([O:16][CH2:17][CH:18]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[C@H:2]([C:11](O)=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH2:31]([NH2:39])[C:32]([NH:34][CH2:35][C:36]([OH:38])=[O:37])=[O:33].C(Cl)(Cl)Cl.CO>C(#N)C>[NH:1]([C:14]([O:16][CH2:17][CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[C:30]1=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:15])[C@H:2]([C:11]([NH:39][CH2:31][C:32]([NH:34][CH2:35][C:36]([OH:38])=[O:37])=[O:33])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 21584188Chloroform methanolHCID 131716513HCID 131716513, compound

Product 1

HCID 14135690HCID 14135690, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

FMOC-Tyr-gly-gly was coupled to ADR as in Section 7.1.1. for gly-ADR. Yield of FMOC-tyr-gly-gly-ADR was 95%; melting point 150°-153° C.; Rf: 0.63 [chloroform/methanol 8:2 (silica); Rf: 0.68 [acetonitrile/0.1% aqueous TFA 1:1 (reverse phase)]. Elemental analysis for C55H54N4O17.H2O; calculated: C, 62.25; H, 5.32; N, 5.30; observed: C, 62.17; H, 5.92; N, 5.09. The protecting FMOC moiety removed from the product as described in Section 7.1.1. for gly-ADR. Yield of the product tyr-gly-gly-ADR.HOAc was 68 mg (80%); melting point, 165° C. (decomp.); Rf: 0.10 [chloroform/methanol 8:2 (silica)]; Rf: 0.53 [acetonitrile 0.1% aqueous TFA 1:1 (reverse phase)]. Elemental analysis for C42H48N4O17.2 H2O; calculated: C, 55.01; H, 5.72; observed: C, 55.15; H, 5.54.

Workup

  1. customThe protecting FMOC moiety removed from the product

Sources & evidence

ORD record
ord-e0453b86f1ef463b87f4fac25b210bcd
Source dataset
uspto-grants-1992_11
Patent number
US05162512

Reaction notes

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