Azido(trimethyl)stannane → Losartan

HRID 2076274Notes

Reaction equation

C[Sn](N=[N+]=[N-])(C)C.[CH3:8][CH2:9][CH2:10][CH2:11][C:12]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[C:29]([C:30]4[N:34]=[N:33][N:32](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:31]=4)=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[C:15]([CH2:54][OH:55])=[C:14]([Cl:56])[N:13]=1>>[CH3:8][CH2:9][CH2:10][CH2:11][C:12]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[C:30]3[N:34]=[N:33][NH:32][N:31]=3)=[CH:20][CH:19]=2)[C:15]([CH2:54][OH:55])=[C:14]([Cl:56])[N:13]=1

Participants

Reactant 2

HCID 5104973Azido(trimethyl)stannane

HCID 10865273Trityllosartan

Product 1

HCID 3961Losartan

Procedure

Dupont/Merck in their patents and papers always described that trityl losartan of the formula (7) is detritylated to get Losartan. They have used trimethyl tin azide or tri alkyl tin azides for the preparation of tetrazoles. The trityl Losartan of the formula (7) is reacted with mineral acid to give Losartan of the formula (1). The trityl Losartan of the formula (7) is prepared using trimethyl or trialkyl tin azide for the formation of tetrazole nucleus.

Sources & evidence

ORD record: ord-33f438bac9234bd2ac3b6c20124e1fdf
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923566B2

Reaction notes

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