Pivaloyl chloride → HCID 44599483, compound

HRID 888529Notes

Reaction equation

C(OC(=O)CC1C=CC(Cl)=C(OC2C=CC(N)=CC=2CSC(C)C)C=1)C.C(Cl)(=O)C(C)(C)C.C([O:36][C:37](=[O:65])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([O:46][C:47]2[CH:52]=[CH:51][C:50]([NH:53][C:54](=[O:59])[C:55]([CH3:58])([CH3:57])[CH3:56])=[CH:49][C:48]=2[CH2:60][S:61][CH:62]([CH3:64])[CH3:63])[CH:40]=1)C>>[Cl:45][C:42]1[CH:43]=[CH:44][C:39]([CH2:38][C:37]([OH:65])=[O:36])=[CH:40][C:41]=1[O:46][C:47]1[CH:52]=[CH:51][C:50]([NH:53][C:54](=[O:59])[C:55]([CH3:58])([CH3:56])[CH3:57])=[CH:49][C:48]=1[CH2:60][S:61][CH:62]([CH3:64])[CH3:63]

Participants

Reactant 3

HCID 62493Pivaloyl chloride

HCID 58372865HCID 58372865, compound

HCID 58372873HCID 58372873, compound

Product 1

HCID 44599483HCID 44599483, compound

Procedure

[3-(2-Bromomethyl-4-nitro-phenoxy)-4-chloro-phenyl]-acetic acid ethyl ester was treated with 2-propanethiol as described in Example 21, Step 8 to provide [4-chloro-3-(2-isopropylsulfanylmethyl-4-nitro-phenoxy)-phenyl]-acetic acid ethyl ester, which was reduced to [3-(4-amino-2-isopropylsulfanylmethyl-phenoxy)-4-chloro-phenyl]-acetic acid ethyl ester as described in Example 21, Step 9. Treatment of the amine with pivaloyl chloride as described in Example 21, Step 10 provided {4-chloro-3-[4-(2,2-dimethyl-propionylamino)-2-isopropylsulfanylmethyl-phenoxy]-phenyl}-acetic acid ethyl ester. Hydrolysis of the ester to the acid was carried out as described in Example 21, Step 11.

Sources & evidence

ORD record: ord-a70af2dbfa7746499a36a3bb49c208a9
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247602B2

Reaction notes

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