Sodium triacetoxyborohydride → 1-cyclopentyl N-[2-(2-{[2,4-bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}-2,3-dihydro-1H-isoindol-5-yl)ethyl]-L-leucinate

HRID 632573

Reaction equation

HRID 632573 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([C:23]([CH3:25])=[CH2:24])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([CH2:37][CH:38]=O)[CH:34]=2)[CH2:29]1)=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:51]1([O:56][C:57](=[O:64])[C@H:58]([CH2:60][CH:61]([CH3:63])[CH3:62])[NH2:59])[CH2:55][CH2:54][CH2:53][CH2:52]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12]([C:23]([CH3:25])=[CH2:24])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([CH2:37][CH2:38][NH:59][C@H:58]([C:57]([O:56][CH:51]3[CH2:52][CH2:53][CH2:54][CH2:55]3)=[O:64])[CH2:60][CH:61]([CH3:62])[CH3:63])[CH:34]=2)[CH2:29]1)=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 86633653L-leucine cyclopentyl ester tosylateHCID 866864242-(2-{[2,4-bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}-2,3-dihydro-1H-isoindol-5-yl)acetaldehyde

Product 1

HCID 866864231-cyclopentyl N-[2-(2-{[2,4-bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}-2,3-dihydro-1H-isoindol-5-yl)ethyl]-L-leucinateYield 53%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of Intermediate F (0.165 g, 0.32 mmol) in dichloroethane (10 mL) was added L-leucine cyclopentyl ester tosylate (0.197 g, 0.52 mmol) and sodium triacetoxyborohydride (0.151 g, 0.71 mmol). The mixture was stirred for 90 minutes, then quenched by addition of saturated ammonium chloride (20 mL). The product was extracted with dichloromethane (3 times 100 mL) and the combined organic extracts were dried (MgSO4), concentrated and purified by flash column chromatography (SiO2, ethyl acetate) to yield the desired product (0.089 g, 53% yield). LC/MS: m/z 701.25 [M+H]+

Workup

  1. customquenched by addition of saturated ammonium chloride (20 mL)
  2. extractionThe product was extracted with dichloromethane (3 times 100 mL)
  3. dry with materialthe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by flash column chromatography (SiO2, ethyl acetate)

Sources & evidence

ORD record
ord-c2cce7aaefb247978e051ebe20dbf00b
Source dataset
uspto-grants-2016_04
Patent number
US09321718B2

Linked notes

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