Diisopropylethylamine → (2S)-4-(((tert-butoxy)carbonyl)amino)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)butanoic acid

HRID 330777

Reaction equation

HRID 330777 reaction equation
C1C=CC(C(Cl)(C2C(Cl)=CC=CC=2)C2C=CC=CC=2)=CC=1.[NH:22]([C:44]([O:46][CH2:47][CH:48]1[C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[C:54]2[C:49]1=[CH:50][CH:51]=[CH:52][CH:53]=2)=[O:45])[C@H:23]([C:41]([OH:43])=[O:42])[CH2:24][CH2:25][N:26](C(OC(C)(C)C)=O)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].CCN(C(C)C)C(C)C>C(Cl)Cl>[NH:22]([C:44]([O:46][CH2:47][CH:48]1[C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[C:54]2[C:49]1=[CH:50][CH:51]=[CH:52][CH:53]=2)=[O:45])[C@H:23]([C:41]([OH:43])=[O:42])[CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 945242-Chlorotrityl chlorideHCID 131728824Fmoc-Dab(diBoc)-OH

Product 1

HCID 2756101(2S)-4-(((tert-butoxy)carbonyl)amino)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)butanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3 g of 2-chlorotrityl chloride resin with 1.3 mmol/g substitution (Novabiochem, 01-64-0114) in 30 ml of dry DCM in 30 ml reaction vessel for solid phase synthesis, 2.577 g (5.85 mmol, 1.5 eq) of Fmoc-Dab(diBoc)-OH (Mw=440.5, (Fmoc-(N-γ-Boc)-L-α,γ-diaminobutyric acid, AnaSpec, 28246) and 2.23 ml (12.87 mmol, 3.3 eq) of DIPEA (Aldrich, Mw=129.2, d=0.74) were added.

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-b8fe60ec7d8e481cb77a9211d1e3495e
Source dataset
uspto-grants-2014_11
Patent number
US08877729B2

Linked notes

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