Acetic Acid → HCID 23257309, compound

HRID 279729Notes

Reaction equation

HRID 279729 reaction equation
[N+](C1C=CC(CCOC([NH:15][C:16]2[C:17]3[N:18]=[CH:19][N:20]([C:52]=3[N:53]=[CH:54][N:55]=2)[C@@H:21]2[O:51][C@H:48]([CH2:49][OH:50])[CH2:47][C@H:22]2[O:23][C:24](=[O:46])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:45])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=O)=CC=1)([O-])=O.C1CCN2C(=NCCC2)CC1.CC(O)=O>N1C=CC=CC=1>[C:31]([NH:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:24]([O:23][C@@H:22]1[CH2:47][C@@H:48]([CH2:49][OH:50])[O:51][C@H:21]1[N:20]1[C:52]2[N:53]=[CH:54][N:55]=[C:16]([NH2:15])[C:17]=2[N:18]=[CH:19]1)=[O:46])(=[O:45])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23257307HCID 23257307, compound

Product 1

HCID 23257309HCID 23257309, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Compound 10 (160 mg, 0.208 mol) was co-evaporated twice with abs. pyridine and then dissolved in abs. pyridine (2 ml). DBU (158 mg, 1.04 mmol) was added, the mixture kept at r.t. for 18 h, then AcOH (62 mg, 1.04 mmol) added, and the soln. evaporated. The residue was diluted with CHCl3 (80 ml) and washed with a 10% citric acid soln. (2×50 ml), the aq. phase reextracted with CHCl3, the combined org. layer dried (MgSO4), evaporated, and co-evaporated with toluene, and the residue precipitated by MeOH and washed with Et2O: 103 mg (86%) of 12. UV (CH2Cl2: 259 (4.16). 1H-NMR ((D6)DMSO): 8.33, 8.13 (2s, H—C(8), H—C(2)); 7.68 (t, NH(CH2)5CO); 7.25 (s, NH2); 6.05 (d, H—C(1′)); 5.60 (m, H—C(2′)); 5.11 (t, OH—C(5′)); 4.32 (m, H—C(4′)); 3.65, 3.47 (2m, 2 H—C(5′)); 2.95 (q, 1 CH2 of NH(CH2)5CO); 2.6, 2.15 (2m, 2 H—C(3′)); 2.34, 2.00 (2t, 2 CH2 of NH(CH2)5CO, 2 H of Me(CH2)12Co); 1.65-1.15 (m, 28 H, 2 CH2 of NH(CH2)5CO, Me(CH2)12CO); 0.83 (t, Me(CH2)12CO). Anal. calc. for C30H50N6O5 ½ H2O (583.76): C 61.72, H 8.81, N. 14.39; found C 62.04, H 9.07, N 13.85.

Workup

  1. customevaporated
  2. additionThe residue was diluted with CHCl3 (80 ml)
  3. washwashed with a 10% citric acid soln
  4. dry with materiallayer dried (MgSO4)
  5. customevaporated
  6. customco-evaporated with toluene, and the residue precipitated by MeOH
  7. washwashed with Et2O

Sources & evidence

ORD record
ord-fb1d6926fe5e4a4db0da8363c12c7f57
Source dataset
uspto-grants-2002_03
Patent number
US06362171B1

Reaction notes

Loading…