Diisopropylethylamine → HCID 67099753, compound

HRID 2078191Notes

Reaction equation

Cl.[NH2:2][CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[Cl:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]1([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[C:17](=[O:27])[C:16]([C:28](OCC)=[O:29])=[C:15]2[OH:33].C(N(C(C)C)C(C)C)C>O1CCOCC1.CCOC(C)=O>[Cl:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]1([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[C:17](=[O:27])[C:16]([C:28]([NH:2][CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[O:29])=[C:15]2[OH:33]

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl 2-aminoacetate hydrochloride (901 mg, 5376 μmol) was added to a mixture of ethyl 6′-chloro-4′-hydroxy-2′-oxo-spiro[cyclohexane-1,1′-naphthalene]-3′-carboxylate (1.20 g, 3584 μmol) in 1,4-dioxane (3584 μL) and N-ethyl-N-isopropylpropan-2-amine (1873 μL, 10753 μmol). The resulting mixture was heated at 80° C. for 2 hours. The resulting mixture was then diluted with 100 mL of EtOAc, added to a separatory funnel, partitioned with NaHCO3 (saturated, aqueous), washed 2 times with 50 mL of NaHCO3 (saturated, aqueous), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (185 mg) as a light yellow solid after purification via preparatory HPLC. MS (m/z)=364 (M+H-tBu)+.

Workup

additionadded to a separatory funnel
custompartitioned with NaHCO3 (saturated, aqueous)
washwashed 2 times with 50 mL of NaHCO3 (saturated, aqueous)
customseparated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3cc68ec55ae049ee974d31a58b317160
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928139B2

Reaction notes

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