Hydrochloric Acid → HCID 86589031, compound

HRID 897052Notes

Reaction equation

HRID 897052 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][C:11]1[N:12]=[CH:13][C:14]([C:17]([OH:19])=[O:18])=[N:15][CH:16]=1.[O:20]1[C@H:22]2[CH2:23][C@@:24]3([CH3:46])[CH:28]([CH:29]4[CH2:30][C@H:31]([F:40])[C:32]5[C@@:37]([CH3:38])([C@:21]124)[CH:36]=[CH:35][C:34](=[O:39])[CH:33]=5)[CH2:27][C@@H:26]([CH3:41])[C@:25]3(O)[C:42]([OH:44])=[O:43].Cl>CN(C=O)C>[O:20]1[C@H:22]2[CH2:23][C@@:24]3([CH3:46])[CH:28]([CH:29]4[CH2:30][C@H:31]([F:40])[C:32]5[C@@:37]([CH3:38])([C@:21]124)[CH:36]=[CH:35][C:34](=[O:39])[CH:33]=5)[CH2:27][C@@H:26]([CH3:41])[C@:25]3([O:18][C:17]([C:14]1[CH:13]=[N:12][C:11]([CH3:10])=[CH:16][N:15]=1)=[O:19])[C:42]([OH:44])=[O:43]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 1228315-Methyl-2-pyrazinecarboxylic acidHCID 49822397HCID 49822397, compound

Product 1

HCID 86589031HCID 86589031, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N,N-Diisopropylethylamine (2.3 mL) is added to a cooled (0° C.) solution of 5-methylpyrazine-2-carboxylic acid (736 mg) in DMF (7 mL), followed by O-(7-azabenzotriazo-1-lyl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 2.26 g). The suspension is stirred at room temperature for 10 minutes, then a solution of (6S,9S,10S,11S,13S,16R,17R)-9,11-epoxy-6-fluoro-17-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid (2 g) in DMF (7 ml) is added. After 2 hours, the reaction mixture is added dropwise to a solution of 1M HCl. The product is collected by filtration, washed repeatedly with water and dried to yield 5-methyl-pyrazine-2-carboxylic acid (6S,9S,10S,11S,13S,16R,17R)-9,11-epoxy-6-fluoro-17-carboxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester. Selected H-NMR signals (CDCl3) δ 0.95 (3H, d), 1.10 (3H, s) 1.40 (3H, s), 2.65 (3H, s).

Workup

  1. waitAfter 2 hours
  2. filtrationThe product is collected by filtration
  3. washwashed repeatedly with water
  4. customdried

Sources & evidence

ORD record
ord-360a41e47bb84774b64a9927d90da324
Source dataset
uspto-grants-2005_07
Patent number
US06921757B2

Reaction notes

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