Water → HCID 58551089, compound

HRID 1908157Notes

Reaction equation

[Cl:1][C:2]1[CH:38]=[CH:37][C:5]2[O:6][C:7]3([C:32]4[N:33]([CH:34]=[CH:35][CH:36]=4)[C:4]=2[CH:3]=1)[CH2:12][CH2:11][N:10]([C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@@H:23]2[CH2:27][O:26]C(C)(C)[O:24]2)=[C:17]([O:30][CH3:31])[CH:16]=1)=[O:14])[CH2:9][CH2:8]3.O.CC1C=CC(S(O)(=O)=O)=CC=1.O>CO>[Cl:1][C:2]1[CH:38]=[CH:37][C:5]2[O:6][C:7]3([C:32]4[N:33]([CH:34]=[CH:35][CH:36]=4)[C:4]=2[CH:3]=1)[CH2:12][CH2:11][N:10]([C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@@H:23]([OH:24])[CH2:27][OH:26])=[C:17]([O:30][CH3:31])[CH:16]=1)=[O:14])[CH2:9][CH2:8]3

Participants

Conditions

Temperature: 80 °C

Procedure

(R)-(8-Chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)(4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-3-methoxyphenyl)methanone (41 mg, 0.076 mmol) and 4-methylbenzenesulfonic acid hydrate (2.9 mg, 0.015 mmol) were dissolved in MeOH (760 μL) and H2O (76 μL) was added. The reaction mixture was heated at 80° C. for 45 min. The mixture was filtered and the residue was purified by reverse phase HPLC using 5 mM HCl/H2O and MeOH to yield (S)-(8-chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)(4-(2,3-dihydroxypropoxy)-3-methoxyphenyl)methanone. ESI-MS m/z calc. 498.2. found 499.3 (M+1)+; Retention time: 4.72 minutes (15 min run).

Workup

filtrationThe mixture was filtered
customthe residue was purified by reverse phase

Sources & evidence

ORD record: ord-9772339e54874e258d5348e98f087c63
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598164B2

Reaction notes

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