Water → Tert-butyl 2-(cyclopropylmethoxy)-4-(hydroxymethyl)phenyl(methylsulfonyl)carbamate

HRID 1776488Notes

Reaction equation

HRID 1776488 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].C1N=CN(C(N2C=NC=C2)=O)C=1.O.[BH4-].[Na+]>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

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydrideHCID 497657284-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoic acid

Product 1

HCID 86679440Tert-butyl 2-(cyclopropylmethoxy)-4-(hydroxymethyl)phenyl(methylsulfonyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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) (200 mg, 0.519 mmol) was dissolved in THF (10.5 ml), then CDI was added (154 mg, 0.95 mmol). The mixture was stirred at RT for 2 days, then H2O (1.75 ml) and NaBH4 (36 mg, 0.95 mmols) were added. The solvent was removed by evaporation under vacuum. The crude was dissolved in EtOAc (80 ml) and washed with water. The organic phase was dried over Na2SO4 and evaporated under vacuum to yield 200 mg of the desired product.

Workup

  1. customThe solvent was removed by evaporation under vacuum
  2. dissolutionThe crude was dissolved in EtOAc (80 ml)
  3. washwashed with water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-71970e318ac24c33bd1a9c9c1d271e0d
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

Loading…