Hexane → HCID 178450805, compound

HRID 2169303Notes

Reaction equation

HRID 2169303 reaction equation
C(O)(=O)C.[C:5]1([C:11]2([CH2:21][C:22]([NH2:24])=[NH:23])[CH2:20][CH2:19][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:25]([O:29][C:30](=[O:45])/[C:31](/O)=[C:32](\[O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)/[C:33](O)=[O:34])([CH3:28])([CH3:27])[CH3:26].C[O-].[Na+].CCCCCC>CO.C(OCC)(=O)C>[C:25]([O:29][C:30]([C:31]1[C:32]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[C:33]([OH:34])[N:24]=[C:22]([CH2:21][C:11]2([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:12][CH2:13][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:19][CH2:20]2)[N:23]=1)=[O:45])([CH3:28])([CH3:26])[CH3:27]

Participants

7

Reactant 4

HCID 8058HexaneHCID 10942334Sodium MethoxideHCID 86725882(E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl esterHCID 867259482-(8-Phenyl-1,4-dioxa-spiro[4.5]dec-8-yl)acetamidine acetic acid salt

Product 1

HCID 178450805HCID 178450805, compoundYield 74.09%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 2-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-yl)-acetamidine acetic acid salt (268) (500 mg, 1.5 mmol) and 2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester 1-methyl ester (4) (553 mg, 1.8 mmol) in methanol (15 mL) were cooled to 0° C., followed by the addition of NaOMe (25% in methanol) (1 mL, 4.5 mmol) and the reaction mixture was stirred at room temperature for 16 h while silica thin layer chromatography was performed (ethyl acetate:hexane=7:3, Rf=0.6). The reaction mixture was diluted with ethyl acetate (40 ml) and washed with brine (2×20 mL). the reaction mixture was subsequently dried and concentrated in vacuo to get a crude mixture which was purified by normal silica gel (100-200 mesh) column chromatography using an eluent gradient (30-50% ethyl acetate in hexane) to obtain pure 5-benzyloxy-6-hydroxy-2-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-ylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (269) (590 mg, 74.09%) as a brown sticky mass.

Workup

  1. washwashed with brine (2×20 mL)
  2. customthe reaction mixture was subsequently dried
  3. concentrationconcentrated in vacuo
  4. customto get a crude mixture which
  5. customwas purified by normal silica gel (100-200 mesh) column chromatography

Sources & evidence

ORD record
ord-ba827a74f22b4ffdbed04a29c52f7d11
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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