Dimethylformamide → HCID 66832680, compound

HRID 579573Notes

Reaction equation

HRID 579573 reaction equation
Cl.Cl.[NH2:3][C@@:4]([C@@H:15]1[CH2:19][CH2:18][NH:17][CH2:16]1)([CH2:8][CH2:9][CH2:10][CH2:11][B:12]([OH:14])[OH:13])[C:5]([OH:7])=[O:6].C(N(CC)CC)C.[CH3:27][N:28](C)[CH:29]=[O:30].[N-]=C=O.[Cl:35][C:36]1[CH:41]=[CH:40]C=[CH:38][CH:37]=1>Cl>[NH2:3][C:4]([C@H:15]1[CH2:19][CH2:18][N:17]([C:29](=[O:30])[NH:28][C:27]2[CH:40]=[CH:41][C:36]([Cl:35])=[CH:37][CH:38]=2)[CH2:16]1)([CH2:8][CH2:9][CH2:10][CH2:11][B:12]([OH:14])[OH:13])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 22244656HCID 22244656, compoundHCID 66833416HCID 66833416, compound

Product 1

HCID 66832680HCID 66832680, compoundYield 6.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (R)-2-amino-6-borono-2-((R)-pyrrolidin-3-yl)hexanoic acid (Example 35-A, Step 5, 200 mg, 0.8 mmol) and triethylamine (900 uL, 6 mmol) in N,N-dimethylformamide (4 mL, 50 mmol) was treated with 4-chlorobenzene isocyanate-(280 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-chlorophenylcarbamoyl)pyrrolidin-3-yl)hexanoic acid (0.021 g, 6%). 1H NMR (400 MHz, D2O, Mixture of diastereoisomers) δ 7.26 (d, J=8.1 Hz, 2H), 7.14 (d, J=8.1 Hz, 2H), 3.70-3.48 (br, m, 2H), 3.99-3.08 (br, m, 2H), 2.79-2.65 (br, m, 1H), 2.30-1.75 (br. m, 4H), 1.54-1.44 (br. m, 2H), 1.35-1.27 (br. m, 1H), 0.87 (t, J=6.5 Hz, 2H),; MS (ESI+) found for C17H25ClBN3O5 m/z (M-water+H)+ 380.2; MS; (M-water+Na)+ 403.3

Workup

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

Sources & evidence

ORD record
ord-889a17ca34db4d28aee5340f401fd533
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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