Ammonia → HCID 11123358, compound

HRID 1584357Notes

Reaction equation

HRID 1584357 reaction equation
O1CCCC1.[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]1[O:12][C:13]([CH3:47])=[C:14]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][C@@H:27]([O:32][C:33]([O:35]C3C=CC([N+]([O-])=O)=CC=3)=O)[C:28]([O:30][CH3:31])=[O:29])=[CH:20][C:19]=2[O:45][CH3:46])[N:15]=1.[NH3:48]>O>[C:33]([O:32][C@H:27]([CH2:26][CH2:25][CH2:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][CH2:16][C:14]2[N:15]=[C:11]([C:7]3[O:6][CH:10]=[CH:9][CH:8]=3)[O:12][C:13]=2[CH3:47])=[C:19]([O:45][CH3:46])[CH:20]=1)[C:28]([O:30][CH3:31])=[O:29])(=[O:35])[NH2:48]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 11734568HCID 11734568, compound

Product 1

HCID 11123358HCID 11123358, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a tetrahydrofuran (THF) (80 ml) solution of methyl (R)-(+)-5-[4-[2-(2-furyl)-5-methyl-4-oxazolyl methoxy]-3-methoxyphenyl]-2-(4-nitrophenoxycarbonyloxy)pentanoate (4.25 g) was introduced ammonia (gas) for 10 minutes at temperature ranging from -65 to -70° C. The reaction mixture was poured into water-6N HCl, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The residue was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-hexane (1:1), was obtained methyl (R)-(+)-2-carbamoyloxy-5-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]pentanoate (3.0 g, 89%), which was recrystallized from acetone-isopropyl ether to give colorless needles, m.p.110-111° C. [α]D +5.30° (c=1. 0, CH3OH)

Workup

  1. customranging from -65 to -70° C
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washFrom the fraction eluted with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-211fe3b81c2d433996b094f6679934a5
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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