HCID 9983548, compound → HCID 10254423, compound

HRID 1294741Notes

Reaction equation

HRID 1294741 reaction equation
C1(NC2C=C([C@@H](N3CCNCC3)C3C=CC(C(N(CC)CC)=O)=CC=3)C=CC=2)CCCCC1.[CH:34]1([NH:40][C:41]2[CH:42]=[C:43]([C@@H:47]([N:61]3[CH2:66][CH2:65][N:64]([CH2:67][CH:68]4CC4)[CH2:63][CH2:62]3)[C:48]3[CH:60]=[CH:59][C:51]([C:52]([N:54]([CH2:57][CH3:58])[CH2:55][CH3:56])=[O:53])=[CH:50][CH:49]=3)[CH:44]=[CH:45][CH:46]=2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>CO>[CH:34]1([NH:40][C:41]2[CH:42]=[C:43]([C@@H:47]([N:61]3[CH2:66][CH2:65][N:64]([CH2:67][CH3:68])[CH2:63][CH2:62]3)[C:48]3[CH:60]=[CH:59][C:51]([C:52]([N:54]([CH2:57][CH3:58])[CH2:55][CH3:56])=[O:53])=[CH:50][CH:49]=3)[CH:44]=[CH:45][CH:46]=2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 9983548HCID 9983548, compoundHCID 10049347HCID 10049347, compound

Product 1

HCID 10254423HCID 10254423, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Synthesized using COMPOUND 27 (250 mg; 0.56 mmol) and the method described for COMPOUND 72. Obtained 163 g; 61% yield. Purity (HPLC-215 nm): >99%; Optical purity (Chiral HPLC-215 nm): >99%. 1H NMR (400 MHz, CD3OD) δ 0.80 (m, 1H), 1.19 (br s, 11H), 1.59 (m, 2H), 1.88 (br s, 5H), 3.14 (br s, 11H), 3.50 (br s, 4H), 4.11 (m, 1H), 7.31 (br s, 3H), 7.67 (br s, 5H). Found: C, 53.63; H, 7.55; N, 8.05. C30H44N4O×5.0HCl×0.7H2O has C, 53.65; H, 7.56; N, 8.34%. [α]D16=+12.7 deg [c 0.50, MeOH].

Workup

  1. customSynthesized
  2. customObtained 163 g

Sources & evidence

ORD record
ord-795acee444ea447bafe02611206c9eef
Source dataset
uspto-grants-2007_07
Patent number
US07241764B2

Reaction notes

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