Water → 2,5-Dioxo-1-pyrrolidinyl (αR)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-2-naphthalenepropanoate

HRID 1921906Notes

Reaction equation

HRID 1921906 reaction equation
[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@@H:2]([C:14]([OH:16])=[O:15])[CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[CH:11]2)=[CH:6][CH:5]=1.C[N:25]1[CH2:30][CH2:29]OCC1.[OH2:31].C[CH:33]([OH:35])[CH3:34]>>[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@@H:2]([C:14]([O:16][N:25]1[C:33](=[O:35])[CH2:34][CH2:29][C:30]1=[O:31])=[O:15])[CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[CH:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 962WaterHCID 3776Isopropanol2×HCID 79724-Methylmorpholine2×HCID 2734481(2R)-2-(((tert-butoxy)carbonyl)amino)-3-(naphthalen-2-yl)propanoic acid

Product 1

HCID 1317297062,5-Dioxo-1-pyrrolidinyl (αR)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-2-naphthalenepropanoateYield 90%

Procedure

Boc-D-2Nal-OH (315.4 g; 1.0 eq.) is dissolved in 2-propanol (6.8 L) at −10° C. and IBC (157 g; 1.15 eq.) and NMM (116 g; 1.15 eq.) is added. After stirring for 5-10 min a mixture of HONSu (230.1 g; 2.0 eq.) in 2-propanol (1.4 L) is added. Additional NMM (10.1 g; 0.1 eq.) is added. After half an hour water (0.82 L) is added to dissolve precipitated NMM.HCl. The product is isolated by filtration, washed with 2-propanol (1 L), and dried. Yield: 90%. HPLC purity: 98.3%.

Workup

  1. additionis added
  2. dissolutionto dissolve
  3. customprecipitated NMM
  4. customThe product is isolated by filtration
  5. washwashed with 2-propanol (1 L)
  6. customdried

Sources & evidence

ORD record
ord-d098f8665e1b4029a4f0883942f28366
Source dataset
uspto-grants-2012_05
Patent number
US08173770B2

Reaction notes

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