3-{[(alpha-Isobutanoyloxyethoxy)carbonyl]aminomethyl]-5-Methylhexanoic Acid → 3-{[(alpha-Isobutanovloxyisobutoxy)carbonyl]aminomethyl]-5-Methyl-Hexanoic Acid

HRID 2415530Notes

Reaction equation

HRID 2415530 reaction equation
C(OC([O:9][C:10]([NH:12][CH2:13][CH:14]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:15][C:16]([OH:18])=[O:17])=[O:11])C)(=O)C(C)C.C(=O)([O-])OC1C=C[CH:28]=[C:27]([CH:31]([O:33][C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])C)[C:26]=1[N+]([O-])=O>>[C:34]([O:33][CH:31]([O:11][C:10]([NH:12][CH2:13][CH:14]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:15][C:16]([OH:18])=[O:17])=[O:9])[CH:27]([CH3:26])[CH3:28])(=[O:38])[CH:35]([CH3:36])[CH3:37]

Participants

3

Reactant 2

HCID 160592343-{[(alpha-Isobutanoyloxyethoxy)carbonyl]aminomethyl]-5-Methylhexanoic AcidHCID 86589559alpha-Isobutanoyloxyethyl-o-Nitrophenyl Carbonate

Product 1

HCID 222720163-{[(alpha-Isobutanovloxyisobutoxy)carbonyl]aminomethyl]-5-Methyl-Hexanoic AcidYield 51%

Procedure

Following the procedure of preparation for (110), and substituting (114) for (111), provided the title compound as a mixture of two diastereomers in 51% yield. 1H-NMR (CDCl3, 400 MHz): δ 0.89 (m, 12H), 1.17 (m, 8H), 1.65 (m, 1H), 2.02 (m, 1H), 2.16 (m, 1H), 2.33 (m, 2H), 2.56 (m, 1H), 3.13 (m, 1H), 3.30 (m, 1H), 5.00 (m, 1H), 6.57-6.56 (m, 1H).

Sources & evidence

ORD record
ord-4a8bca8c7bde4a9da887c2f8527c246c
Source dataset
uspto-grants-2004_11
Patent number
US06818787B2

Reaction notes

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