Neoviridogrisein IV → N-Methyl-N-phenyl-glycine

HRID 223586

Reaction equation

HRID 223586 reaction equation
C[C@H]1OC(=O)[C@H]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)N(C)C(=O)[C@H](C)NC(=O)C([C@H](C(C)C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2N(C[C@H](O)C2)C(=O)[C@@H](CC(C)C)NC(=O)[C@H]1NC(C1N=CC=CC=1O)=O.CC1[O:96][C:94](=[O:95])[CH:93](C2C=CC=CC=2)[N:92](C)[C:90](=O)C(C)NC(=O)C(C(C(C)C)C)N(C)C(=O)CN(C)C(=O)C2N(CC(O)C2)C(=O)C(CC(C)C)NC(=O)C1NC(C1N=CC=CC=1O)=O.C[C@H]1OC(=O)[C@H]2CSC(C(NCC=CC=C[C@@H](O)C[C@@H](O)CC3OC=C(C(N2)=O)N=3)=O)=CC1>>[C:34]1([N:92]([CH2:93][C:94]([OH:96])=[O:95])[CH3:90])[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

4

Reactant 3

HCID 196972Neoviridogrisein IVHCID 4172563-Hydroxy-N-(24-Hydroxy-7,11,13,17,20-Pentamethyl-16-(3-Methylbutan-2-Yl)-3-(2-Methylpropyl)-2,5,9,12,15,18,21-Heptaoxo-10-Phenyl-8-Oxa-1,4,11,14,17,20-Hexazabicyclo(20.3.0)Pentacosan-6-Yl)Pyridine-2-CarboxamideHCID 6441064(1S,9R,11S,12Z,14Z,19Z,22R)-9,11-Dihydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.14,7]heptacosa-4,7(27),12,14,19-pentaene-3,18,24-trione2×

Product 1

HCID 420843N-Methyl-N-phenyl-glycine

Procedure

In addition the identity of neoviridogrisein IV with viridogrisein was further confirmed by IR, UV, NMR and mass spectrometry, thin layer chromatography, hydrolysate analysis and antimicrobial spectrometry. On the other hand, the griseoviridin preparation obtained in Example 5 was crystallized in warm methanol to yield needle crystals. Then a part of the needle crystals were compared and identified with an authentic preparation of griseoviridin by IR, UV, NMR and mass spectrometry, thin layer chromatography, elementary analysis and other physico-chemical properties.

Workup

  1. customobtained in Example 5
  2. customwas crystallized in warm methanol
  3. customto yield needle crystals

Sources & evidence

ORD record
ord-517422c010fe47a2a29a2371a659c8a6
Source dataset
uspto-grants-1982_10
Patent number
US04355112

Linked notes

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