Acetic Acid → HCID 71598080, compound

HRID 405087Notes

Reaction equation

HRID 405087 reaction equation
[CH3:1][C@:2]12[C@@:19]3([CH3:20])[C@@H:10]([C@:11]4([CH3:32])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:22])([CH3:21])[C:14]([C:23]3[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=3)=[CH:13][CH2:12]4)[CH2:9][CH2:8][C@@H:7]1[C@H:6]1[C@H:33]([C:36]([CH3:38])=[CH2:37])[CH2:34][CH2:35][C@:5]1([CH2:39][NH:40][C:41](=[O:45])[CH2:42][NH:43][CH3:44])[CH2:4][CH2:3]2.C=O.[C:48](O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:44][N:43]([CH3:48])[CH2:42][C:41]([NH:40][CH2:39][C@:5]12[CH2:35][CH2:34][C@@H:33]([C:36]([CH3:38])=[CH2:37])[C@@H:6]1[C@@H:7]1[C@@:2]([CH3:1])([CH2:3][CH2:4]2)[C@@:19]2([CH3:20])[C@@H:10]([C@:11]3([CH3:32])[C@@H:16]([CH2:17][CH2:18]2)[C:15]([CH3:21])([CH3:22])[C:14]([C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1)=[O:45]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 71598470HCID 71598470, compound

Product 1

HCID 71598080HCID 71598080, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(methylamino)acetamido)methyl)-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid, example 139, (10 mg, 0.016 mmol) and formaldehyde (0.488 mg, 0.016 mmol) in MeOH (1 ml) was added acetic acid (1.860 mL, 0.033 mmol) and sodium cyanoborohydride (1.022 mg, 0.016 mmol). A clear solution was formed soon after mixing. The mixture was stirred at rt for 2 h, LC/MS showed the mass of the expected product. The mixture was diluted with 7 ml of sat. NaHCO3 and was extracted with dichloromethane (3×7 ml). The combined organic layers were dried with Na2SO4. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to afford the title compound as a white solid (2 mg, 18.6%). LCMS: m/e 629.4 (MH+), 2.72 min (method 3). 1H NMR (400 MHz, MeOD) δ ppm 7.90 (d, J=8.6 Hz, 2H), 7.20 (d, J=8.3 Hz, 2H), 5.19-5.42 (m, 1H), 4.72 (d, J=1.8 Hz, 1H), 4.59 (s, 1H), 3.93 (s, 2H), 3.58 (br. s., 1H), 3.04-3.17 (m, 1H), 2.89 (s, 6H), 2.46-2.60 (m, 1H), 2.10-2.18 (m, 2H), 1.80 (br. s., 2H), 1.65-1.77 (m, 7H), 1.63 (s, 1H), 1.58 (br. s., 2H), 1.38-1.55 (m, 4H), 1.19-1.34 (m, 4H), 1.13-1.19 (m, 4H), 1.06-1.13 (m, 2H), 1.04 (s, 3H), 1.02 (s, 3H), 0.95 (s, 3H), 0.93 (s, 3H).

Workup

  1. customA clear solution was formed soon
  2. additionafter mixing

Sources & evidence

ORD record
ord-404e056bf9a74911b665c0e0b9443529
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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