4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoic acid → Tert-butyl 2-(cyclopropylmethoxy)-4-(hydroxymethyl)phenyl(methylsulfonyl)carbamate

HRID 1776636Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][C:14]=1[O:22][CH2:23][CH:24]1[CH2:26][CH2:25]1)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[CH:24]1([CH2:23][O:22][C:14]2[CH:15]=[C:16]([CH2:17][OH:18])[CH:20]=[CH:21][C:13]=2[N:8]([S:9]([CH3:12])(=[O:11])=[O:10])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:26][CH2:25]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoic acid (for reference procedure see Example 18, WO 2010/089107, which is incorporated herein by reference in its entirety) (0.500 g, 1.297 mmol) in anhydrous THF (10 ml), BH3*THF complex (1M solution in THF, 2.59 ml, 2.59 mmol) was added drop wise at RT under nitrogen atmosphere. After 4 hours, the reaction was cooled to 0° C. and quenched with aqueous NH4Cl. The mixture was extracted with EtOAc and the organic phase was dried over Na2SO4 and evaporated under reduced pressure affording tert-butyl 2-(cyclopropylmethoxy)-4-(hydroxymethyl)phenyl(methylsulfonyl)carbamate as a colorless oil (0.430 g, 1.158 mmol, 89% yield, MS/ESI+ 394.2 [MNa]+). This product was used without purification.

Workup

customquenched with aqueous NH4Cl
extractionThe mixture was extracted with EtOAc
dry with materialthe organic phase was dried over Na2SO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-9175689ef8e94951a77d5dbe1b7820ee
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265768B2

Reaction notes

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