Hexane → HCID 178441512, compound

HRID 2255548Notes

Reaction equation

HRID 2255548 reaction equation
[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:32](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:31]=[N:30][N:29]=3)=[CH:18][CH:17]=2)[C:13](=[O:52])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:53][C:54]([O:56][CH2:57][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[O:55])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].CCCCCC>C(O)(=O)C>[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[NH:29][N:30]=[N:31][N:32]=3)=[CH:20][CH:21]=2)[C:13](=[O:52])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:53][C:54]([O:56][CH2:57][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[O:55])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8058HexaneHCID 131718097HCID 131718097, compound

Product 1

HCID 178441512HCID 178441512, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The product of Example 44 was deprotected in the manner described in Example 69. The product was purified by MPLC over a silica Lobar A column eluting with 40:59:1 EtOAc:hexane:acetic acid to give a 55% yield of a white solid. 1H-NMR (CDCl3, 300 MHz): 0.87 (t, 3H, J=7.4 Hz), 1.32 (m, 2H), 1.69 (m, 2H), 2.65 (3 line m, 2H, J=7.3 Hz), 5.15 (s, 2H), 5.29 (bs, 2H), 6.95 and 7.04 (AB, 4H, J=8.2 Hz), 7.30-7.42 (m, 5H), 7.49-7.59 (m, 3H), 7.72(bs, 1H), 7.98 (d, 1H), 8.06 (s, 1H), 8.12 (bd, 1H). FABMS m/e: 586 (M+ +1) calc. for C34H31N7O3

Workup

  1. customThe product was purified by MPLC over a silica Lobar A column
  2. washeluting with 40:59:1 EtOAc

Sources & evidence

ORD record
ord-5bff8ece838a457c85c09c9dba8d8e08
Source dataset
uspto-grants-1993_08
Patent number
US05240928

Reaction notes

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