4-Acetylamino-4-(2-tert-butoxycarbonyl-ethyl)-heptanedioic acid di-tert-butyl ester → 4-Acetylamino-4-(2-carboxy-ethyl)-heptanedioic acid

HRID 2280242Notes

Reaction equation

HRID 2280242 reaction equation
C([O:5][C:6](=[O:32])[CH2:7][CH2:8][C:9]([NH:28][C:29](=[O:31])[CH3:30])([CH2:19][CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])[CH2:10][CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])(C)(C)C>C(O)=O>[C:29]([NH:28][C:9]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH2:8][CH2:7][C:6]([OH:32])=[O:5])(=[O:31])[CH3:30]

Participants

3

Reactant 1

HCID 867110904-Acetylamino-4-(2-tert-butoxycarbonyl-ethyl)-heptanedioic acid di-tert-butyl ester

Product 1

HCID 534735204-Acetylamino-4-(2-carboxy-ethyl)-heptanedioic acidYield 93%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

1.5 g of triester 63 (3.28 mmol) was added to 20 ml formic acid (96%) and stirred for 4 hours. After this time the formic acid was removed by azeotropic distillation with 5×20 ml portions of toluene. The crude residue was recrystallised from EtOH and petroleum spirit to give 0.9 g of off white crystals in 93% yield.

Workup

  1. customAfter this time the formic acid was removed by azeotropic distillation with 5×20 ml portions of toluene
  2. customThe crude residue was recrystallised from EtOH and petroleum spirit
  3. customto give 0.9 g of off white crystals in 93% yield

Sources & evidence

ORD record
ord-9f5f4ef5b055472eb07a5a025e199a83
Source dataset
uspto-grants-2015_09
Patent number
US09138495B2

Reaction notes

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