Benzyloxycarbonylglycine → HCID 131721789, compound

HRID 1106954Notes

Reaction equation

HRID 1106954 reaction equation
[NH:1]([C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH2:2][C:3]([OH:5])=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C1C=CC2N(O)N=NC=2C=1.[NH2:53][C@H:54]([C:67]([N:69]1[CH2:80][CH2:79][CH2:78][C@H:70]1[C:71]([O:73][C:74]([CH3:77])([CH3:76])[CH3:75])=[O:72])=[O:68])[CH2:55][CH2:56][CH2:57][CH2:58][NH:59][C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61]>CN(C=O)C.C(Cl)Cl>[NH:1]([C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH2:2][C:3]([NH:53][C@H:54]([C:67]([N:69]1[CH2:80][CH2:79][CH2:78][C@H:70]1[C:71]([O:73][C:74]([CH3:77])([CH3:76])[CH3:75])=[O:72])=[O:68])[CH2:55][CH2:56][CH2:57][CH2:58][NH:59][C:60]([O:62][C:63]([CH3:65])([CH3:66])[CH3:64])=[O:61])=[O:5]

Participants

6

Reactant 4

HCID 14349BenzyloxycarbonylglycineHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 14010669H-Lys(Boc)-Pro-OtBu

Product 1

HCID 131721789HCID 131721789, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

C] Z-Gly-OH (0.762 g, 3.64 mmoles) was dissolved in 15 ml of DMF/methylene chloride (1:1 v/v) and sequentially added with BOP (1.61 go 3.64 mmoles), HOBT (0.491 g, 3.64 mmoles), TEA (1.01 ml, 7.28 mmoles) and H-Lys(Boc)-Pro-OtBu (1.119 g, 2.8 mmoles) dissolved in 15 ml of the same mixture. The reaction mixture was treated as described under A]. There were obtained 1.16 g of Z-Gly-Lys(Boc)-Pro-OtBu.

Workup

  1. additionThe reaction mixture was treated

Sources & evidence

ORD record
ord-8deae65b5d2d4fd2ab18cb72b1f8d513
Source dataset
uspto-grants-2000_05
Patent number
US06057295

Reaction notes

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