Potassium Carbonate → (S)-4-(tert-butoxycarbonylamino)-6-chlorothiochromane-7-carboxylic acid

HRID 585758Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([C@@H:9]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:11][S:12]2)=[CH:7][C:6]=1[Cl:23])=[O:4].C(=O)([O-])[O-].[K+].[K+]>>[C:19]([O:18][C:16]([NH:15][C@@H:9]1[C:8]2[C:13](=[CH:14][C:5]([C:3]([OH:4])=[O:2])=[C:6]([Cl:23])[CH:7]=2)[S:12][CH2:11][CH2:10]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

Reactant 2

HCID 11430Potassium Carbonate

HCID 59089434(S)-4-(tert-butoxycarbonylamino)-6-chlorothiochromane-7-carboxylic acid methyl ester

Product 1

HCID 59089433(S)-4-(tert-butoxycarbonylamino)-6-chlorothiochromane-7-carboxylic acidYield 87.1%

Procedure

By a similar reaction operation as in Starting Material Synthetic Example 6 using (S)-4-(tert-butoxycarbonylamino)-6-chlorothiochromane-7-carboxylic acid methyl ester (1.10 g) and potassium carbonate (847 mg), the objective (S)-4-(tert-butoxycarbonylamino)-6-chlorothiochromane-7-carboxylic acid (921 mg) was obtained as colorless crystals.

Sources & evidence

ORD record: ord-457c7b7d47e14f559d6fca5707853da1
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06933305B2

Reaction notes

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