2-Bromo-3,3-dimethylbutanoic Acid → 2-tert-butyl-N-[2-(1-adamantylthio)ethyl-]glycine

HRID 329216

Reaction equation

HRID 329216 reaction equation
[C:1]12([S:11][CH2:12][CH2:13][NH2:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C[O-].[Na+].Br[CH:19]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:20]([OH:22])=[O:21]>C(O)(C)(C)C>[C:23]([CH:19]([C:20]([OH:22])=[O:21])[NH:14][CH2:13][CH2:12][S:11][C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2)([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 1842512-Bromo-3,3-dimethylbutanoic AcidHCID 3037992-(Adamantan-1-ylthio)ethanamineHCID 10942334Sodium Methoxide

Product 1

HCID 214390332-tert-butyl-N-[2-(1-adamantylthio)ethyl-]glycine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 42.3 parts of 2-(1-adamantylthio)ethylamine, 10.8 parts of sodium methoxide, 39.0 parts of 2-bromo-2-tert-butyl acetic acid and 315 parts of tert-butanol is refluxed, under a nitrogen atmosphere, for 5 hours. The product is recovered in the manner described in Example 5 to yield 2-tert-butyl-N-[2-(1 -adamantylthio)ethyl-]glycine, melting at about 220°-230°.

Workup

  1. temperatureis refluxed, under a nitrogen atmosphere, for 5 hours
  2. customThe product is recovered in the manner

Sources & evidence

ORD record
ord-49abff0ab6134960a4a17e04072b4618
Source dataset
uspto-grants-1977_04
Patent number
US04020079

Linked notes

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