Isovaleryl chloride → 3-(Isovaleryloxy)-4-(pivalyloxy)phenyl tert-butylaminomethyl ketone

HRID 1390452Notes

Reaction equation

[C:1]([NH:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[C:11]([OH:22])[CH:10]=1)=[O:8])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].C1([O-])C=CC=CC=1.[Na+].[C:34](Cl)(=[O:39])[CH2:35][CH:36]([CH3:38])[CH3:37]>>[C:1]([NH:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[C:11]([O:22][C:34](=[O:39])[CH2:35][CH:36]([CH3:38])[CH3:37])[CH:10]=1)=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 4

HCID 66054Isovaleryl chloride

HCID 4445035Phenolate Sodium

HCID 10942334Sodium Methoxide

HCID 122950163-Hydroxy-4-(pivalyloxy)phenyl tert-butylaminomethyl ketone

Product 1

HCID 130807723-(Isovaleryloxy)-4-(pivalyloxy)phenyl tert-butylaminomethyl ketone

Procedure

Following a procedure similar to that described in Example 2A above, when 3-hydroxy-4-(pivalyloxy)phenyl tert-butylaminomethyl ketone is interacted with one equivalent of sodium methoxide and the resulting sodium phenolate salt is reacted with isovaleryl chloride there is obtained 3-(isovaleryloxy)-4-(pivalyloxy)phenyl tert-butylaminomethyl ketone, which reacts with hydrochloric acid to yield the hydrochloride salt as a white crystalline solid, m.p. 216-220° C. (uncorr.).

Sources & evidence

ORD record: ord-0e75cb17f5c9441b835c61d18df20bb2
Source dataset: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04138581

Reaction notes

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