Cyclopentanol → [4-(5-Cyclopentyloxy-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester

HRID 403467

Reaction equation

HRID 403467 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[O:17][C:18]3[N:19]=[C:20](S(C)(=O)=O)[N:21]=[C:22]([O:25][CH2:26][CH2:27][CH3:28])[C:23]=3[N:24]=2)=[CH:11][C:10]=1[CH3:33])([CH3:4])([CH3:3])[CH3:2].[CH:35]1([OH:40])[CH2:39][CH2:38][CH2:37][CH2:36]1.C(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(C)(C)C>>[C:1]([O:5][C:6](=[O:34])[CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[O:17][C:18]3[N:19]=[C:20]([O:40][CH:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)[N:21]=[C:22]([O:25][CH2:26][CH2:27][CH3:28])[C:23]=3[N:24]=2)=[CH:11][C:10]=1[CH3:33])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 7298CyclopentanolHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneHCID 86679896Tert-butyl [4-(5-methanesulfonyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]acetate

Product 1

HCID 86679898[4-(5-Cyclopentyloxy-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl esterYield 27.2%

Conditions

Temperature
100 °C

Procedure

A solution of 98 mg of [4-(5-methanesulfonyl-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester, 19 mg of cyclopentanol and 69 mg of (tert-butylimino)tris(pyrrolidino)phosphorane was reacted at room temperature for 16 h and subsequently heated in a microwave reactor to 100° C. for 10 min. The mixture was poured onto water and extracted twice with ethyl acetate. The combined organic layers were washed with a 10% aqueous solution of citric acid and brine, dried and evaporated. After purification by preparative HPLC, 27 mg of the title compound were obtained.

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with a 10% aqueous solution of citric acid and brine
  4. customdried
  5. customevaporated
  6. customAfter purification by preparative HPLC

Sources & evidence

ORD record
ord-31c921d7ce224a1fae567d02eb829044
Source dataset
uspto-grants-2014_06
Patent number
US08748436B2

Linked notes

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