Hydrochloric Acid → HCID 67071550, compound

HRID 874293Notes

Reaction equation

HRID 874293 reaction equation
C[O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:14][N:13]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:12]1)[CH2:10][C:9]2=[O:28].Cl>CC(O)=O>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][CH2:15][N:13]2[CH2:14][C:11]3([CH2:10][C:9](=[O:28])[C:8]4[C:25](=[CH:26][CH:27]=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:29])=[O:2])[CH:7]=4)[O:24]3)[CH2:12]2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67071507HCID 67071507, compound

Product 1

HCID 67071550HCID 67071550, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(E)-3-{1′-[2-(4-Fluoro-phenyl)-ethyl]-4-oxo-spiro(chromane-2,3′-azetidine)-6-yl}-acrylic acid methyl ester (120 mg, 0.30 mmol) was hydrolyzed in AcOH (10 ml) and 20% aqueous HCl solution (10 ml) following the procedure described in Example 31, Step B, giving (E)-3-{1′-[2-(4-fluoro-phenyl)-ethyl]-4-oxo-spiro(chromane-2,3′-azetidine)-6-yl}-acrylic acid as a yellow solid. [LC-MS: (ES+) MH+: 382]. The obtained acid was suspended in DCM (5 ml), treated with TEA (0.06 ml, 0.4 mmol) and then with EDC (86 mg, 0.45 mmol), HOBt (61 mg, 0.45 mmol) and NH2OTHP (42 mg, 0.36 mmol) following the procedure described in Example 30, Step B, giving (E)-3-{1′-[2-(4-fluoro-phenyl)-ethyl]-4-oxo-spiro(chromane-2,3′-azetidine)-6-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide (88 mg) as a light yellow solid.

Sources & evidence

ORD record
ord-8b8965af2ff54bce9266870a5d49535c
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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