Reaktion #90989

ord-32f766646775416f9a3e8ff1d41d5483

Reaktionsgleichung

COC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)CCCCCNC(=O)OC(C)(C)C
9-methyl 13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oate
COC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)CCCCCNC(=O)OC(C)(C)C
(S)-methyl 13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oate
O.[Li][OH]
LiOH.H2O
→
CC(C)C[C@H](NC(=O)CCCCCNC(=O)OC(C)(C)C)C(=O)NCC(=O)O
(S)-13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oic acid

Edukte

COC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)CCCCCNC(=O)OC(C)(C)C
9-methyl 13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oate
COC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)CCCCCNC(=O)OC(C)(C)C
(S)-methyl 13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oate
O.[Li][OH]
LiOH.H2O

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF
O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenthe reaction mixture was concentrated
  2. 2
    workup.ADDITIONdiluted with water
  3. 3
    Sonstigethe white precipitate formed
  4. 4
    Filtrationwas filtered off
  5. 5
    Waschenrinsed with water
  6. 6
    Sonstigedried

Vorschrift

To a solution of (9-methyl 13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oate (6w) in THF was added a solution of LiOH.H2O in water at room temperature. After 3 h, the reaction mixture was concentrated, diluted with water and acidified with a 1N aqueous solution of HCl to about pH 4-5. The mixture was stirred for 15 min and the white precipitate formed was filtered off, rinsed with water, and dried to afford (S)-13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oic acid (7w).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09447030B2uspto-grants-2016_09