Potassium Carbonate → HCID 59916625, compound

HRID 993144Notes

Reaction equation

HRID 993144 reaction equation
C([O:4][CH2:5][C:6]1[N:7]=[C:8]([NH:11][C@H:12]([C:20]([NH:22][C@@H:23]([CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C@H:24]([OH:43])[CH2:25][N:26]2[C@H:35]([C:36]([NH:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:34][C@H:33]3[C@H:28]([CH2:29][CH2:30][CH2:31][CH2:32]3)[CH2:27]2)=[O:21])[C:13]([S:16]([CH3:19])(=[O:18])=[O:17])([CH3:15])[CH3:14])[S:9][CH:10]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[C:39]([NH:38][C:36]([C@@H:35]1[CH2:34][C@H:33]2[C@H:28]([CH2:29][CH2:30][CH2:31][CH2:32]2)[CH2:27][N:26]1[CH2:25][C@@H:24]([OH:43])[C@@H:23]([NH:22][C:20](=[O:21])[C@H:12]([C:13]([S:16]([CH3:19])(=[O:18])=[O:17])([CH3:15])[CH3:14])[NH:11][C:8]1[S:9][CH:10]=[C:6]([CH2:5][OH:4])[N:7]=1)[CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:37])([CH3:40])([CH3:41])[CH3:42]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59916581HCID 59916581, compound

Product 1

HCID 59916625HCID 59916625, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A stirred solution of 73 mg (0.1 mmol) of 2-[3(S)-[[N-[4-(acetoxymethyl)-2-thiazolyl]-3-(methanesulfonyl)-L-valyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert-butyl-1,2,3,4,4a(S),5,6,7,8,8a(S)-decahydro-3(S)-isoquinolinecarboxamide (Example 141) in 7 ml of methanol/water (5:2) was treated with 700 mg of potassium carbonate. After 1.5 hours the volatiles were evaporated and the residue partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate and the combined organic phase was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give a gum which was chromatographed on silica eluting with dichloromethane/methanol (40:3) to give 32 mg (48%) of N-tert-butyl-1,2,3,4,4a(S),5,6,7,8,8a(S)-decahydro-2-[2(R)-hydroxy-3(S)-[[N-[4-(hydroxymethyl)-2-thiazolyl]-3-(methanesulfonyl)-L-valyl]amino]-4-phenylbutyl]-3(S)-isoquinolinecarboxamide as a solid, mp 126° C., [M+H]+ 692.

Workup

  1. customAfter 1.5 hours the volatiles were evaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto give a gum which
  8. customwas chromatographed on silica eluting with dichloromethane/methanol (40:3)

Sources & evidence

ORD record
ord-ceefa72ef7b1407da59424a75ad8dc1a
Source dataset
uspto-grants-2002_10
Patent number
US06472404B1

Reaction notes

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