HCID 59547330, compound → HCID 59547347, compound

HRID 2038570Notes

Reaction equation

[C:1]([O:5][C:6]([C@@H:8]1[CH2:24][C@:11]2([O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[CH2:12]2)[CH2:10][NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:25]1([CH2:31][C:32]([NH:34][C@@H:35]([C:39]([CH3:42])([CH3:41])[CH3:40])[C:36](O)=[O:37])=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>>[C:1]([O:5][C:6]([C@@H:8]1[CH2:24][C@:11]2([O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[CH2:12]2)[CH2:10][N:9]1[C:36](=[O:37])[C@@H:35]([NH:34][C:32](=[O:33])[CH2:31][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[C:39]([CH3:41])([CH3:42])[CH3:40])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 59547330HCID 59547330, compound

HCID 61144094HCID 61144094, compound

Product 1

HCID 59547347HCID 59547347, compoundYield 46.2%

Procedure

Following the procedure from Example 1 step G using (5S,8S)-tert-butyl-3-(3-chlorophenyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylate (B5) (32 mg, 91 μmol, 1 eq.) and (5)-2-(2-cyclohexylacetamido)-3,3-dimethylbutanoic acid (25 mg, 100 μmol, 1.2 eq.) gave 25 mg (42 μmol) of (5S,8S)-tert-butyl-3-(3-chlorophenyl)-7-((S)-2-(2-cyclohexylacetamido)-3,3-dimethylbutanoyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylate (C5). LC MS+/−: 590.31/589.47 at 3.95 min (10-90%, 3-5 min, Formic Acid).

Sources & evidence

ORD record: ord-c360961360814d1fa6085d9fa1358843
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575208B2

Reaction notes

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