tert-Butanol → HCID 131727649, compound

HRID 1817359Notes

Reaction equation

HRID 1817359 reaction equation
C([N:3]1[C:12](=[O:13])C(OC)=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[C:20]([Cl:25])[CH:19]=3)[C:9]2=[O:16])=[C:4]1C(O)=O)C.[CH:29]([N:32](C(C)C)CC)(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[O:55]1[CH2:60][CH2:59][O:58][CH2:57]C1.[C:61]([OH:65])([CH3:64])([CH3:63])[CH3:62]>>[C:61]([O:65][C:12](=[O:13])[NH:3][C:4]1[N:32]([CH3:29])[C:60](=[O:55])[C:59]([O:58][CH3:57])=[C:10]2[C:5]=1[CH2:6][CH2:7][N:8]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]([Cl:25])[CH:19]=1)[C:9]2=[O:16])([CH3:64])([CH3:63])[CH3:62]

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 69061026HCID 69061026, compound

Product 1

HCID 131727649HCID 131727649, compound

Conditions

Temperature
90 °C

Procedure

A solution of ethyl 6-(3-chloro-4-fluorobenzyl)-4-methoxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylic acid (1.2 g, 3.04 mmol; Example 12, step 12), diisopropylethylamine (0.37 g, 3.65 mmol), and diphenylphosphoryl azide (1.00 g, 3.65 mmol) in a 1:1 mixture of dioxane and tert-butanol (30 mL) was heated in an oil bath 90° C. for 3 hours. The reaction mixture was concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 5% methanol in dichloromethane. Collection and concentration of appropriate fractions provided the titled compound.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-70b8656cd8bf409eb888898bc7847a56
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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