Dimethylformamide → HCID 86663733, compound

HRID 579572Notes

Reaction equation

HRID 579572 reaction equation
[NH2:1][C@@:2]([C@@H:13]1[CH2:17][CH2:16][NH:15][CH2:14]1)([CH2:6][CH2:7][CH2:8][CH2:9][B:10]([OH:12])[OH:11])[C:3]([OH:5])=[O:4].C(N(CC)CC)C.CN(C)C=O.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([N:37]=[C:38]=[S:39])=[CH:33][CH:32]=1>Cl>[ClH:30].[ClH:30].[NH2:1][C:2]([C@H:13]1[CH2:17][CH2:16][N:15]([C:38](=[S:39])[NH:37][C:34]2[CH:35]=[CH:36][C:31]([Cl:30])=[CH:32][CH:33]=2)[CH2:14]1)([CH2:6][CH2:7][CH2:8][CH2:9][B:10]([OH:12])[OH:11])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 164804-Chlorophenyl isothiocyanateHCID 66833417HCID 66833417, compound

Product 1

HCID 86663733HCID 86663733, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (R)-2-amino-6-borono-2-((R)-pyrrolidin-3-yl)hexanoic acid (200 mg, 0.8 mmol) and triethylamine (700 mg, 6 mmol) in N,N-dimethylformamide (4 mL, 50 mmol) was treated with 4-chlorophenyl isothiocyanate (300 mg, 1.8 mmol) in a single portion. After stirring at room temperature for 30 min, the reaction was diluted with 1 N HCl (20 mL) and washed with ethyl acetate (20 mL). The aqueous solution was concentrated and purified by HPLC to give 2-amino-6-borono-2-((S)-1-(4-chlorophenylcarbamothioyl)pyrrolidin-3-yl)hexanoic acid hydrochloride hydrochloride (81 mg, 20%). 1H NMR (400 MHz, D2O, Mixture of diastereoisomers) δ 7.40-7.23 (m, 4H), 4.29-3.46 (m, 4H), 2.95-2.81 (m, 1H), 2.41-1.76 (m, 4H), 1.58-1.40 (br. m, 2H), 1.36-1.20 (br, m, 1H), 0.90-0.80 (br. m, 2H); MS ESI found for C17H25BClN3O4S m/z (M-water+H)+396.2; MS (ESI−) m/z (M−H)− 412.3, (M-water-H)− 394.3

Workup

  1. washwashed with ethyl acetate (20 mL)
  2. concentrationThe aqueous solution was concentrated
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-54dcafbdfb994498adb5938d625c2bc4
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

Loading…