Water → HCID 135674092, compound

HRID 392984Notes

Reaction equation

HRID 392984 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:30]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[C:16]3=[N:17][CH:18]=[C:19]([C:21]4[N:25]([CH2:26][CH2:27][C:28]#[N:29])[N:24]=[N:23][N:22]=4)[CH:20]=[C:15]3[N:14]=2)=[CH:9][CH:8]=1)(C)(C)C.O.C(OCC)(=O)C>C(O)(=O)C.O1CCCC1>[CH:31]1([N:30]2[C:16]3=[N:17][CH:18]=[C:19]([C:21]4[N:25]([CH2:26][CH2:27][C:28]#[N:29])[N:24]=[N:23][N:22]=4)[CH:20]=[C:15]3[N:14]=[C:13]2[C:10]2[CH:9]=[CH:8][C:7]([OH:6])=[CH:12][CH:11]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 22660825HCID 22660825, compound

Product 1

HCID 135674092HCID 135674092, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of intermediate 62 (78 mg, 0.15 mmol) in glacial acetic acid (3 mL), tetrahydrofuran (1 mL), and water (1 mL) was heated to 100° C. for 3 h under a nitrogen atmosphere. Ethyl acetate (40 mL) was added and the organic phase washed with water (2×20 mL), NaHCO3 (2×20 mL), and brine (1×). The organic phase was dried (Na2SO4) and concentrated on a rotary evaporator to afford intermediate 63 as a white solid (54 mg, 89%). ESI-MS m/e 415.1 (M+1).

Workup

  1. washthe organic phase washed with water (2×20 mL), NaHCO3 (2×20 mL), and brine (1×)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-f9ed40b64f544d7ca42703036130d14a
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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