Ammonia → HCID 57188993, compound

HRID 1751159Notes

Reaction equation

HRID 1751159 reaction equation
[NH:1]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@H:2]([C:24](O)=[O:25])[CH2:3][S:4][C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1CCC([N:40]=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.N>C(Cl)Cl.CN(C)C=O>[NH:1]([C:27]([O:29][C:30]([CH3:33])([CH3:31])[CH3:32])=[O:28])[C@H:2]([C:24]([NH2:40])=[O:25])[CH2:3][S:4][C:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 11167161N-((1,1-Dimethylethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteine

Product 1

HCID 57188993HCID 57188993, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of Boc-Cys(Trt)-OH (100 gm) in methylene chloride (1000 ml) at −10 to 0° C., was charged sequentially, a solution of DCC (57.9 g) in methylene chloride (125 ml) and HOBT (34.8 gm) in dimethyl formamide (70 ml). Stirred the solution for 30 minutes at the same temperature and then charged ammonia solution (120 ml). After completion of the reaction the resultant precipitate was filtered and the filtrate was taken and washed with 10% sodium bicarbonate solution. The separated organic layer was concentrated and crystallized the product Boc-Cys(Trt)-NH2 from ethyl acetate and hexane (Yield: 100 g, HPLC Purity 98%, Chiral purity: 99.9% and D-Cys: 0.1%).

Workup

  1. filtrationwas filtered
  2. washwashed with 10% sodium bicarbonate solution
  3. concentrationThe separated organic layer was concentrated
  4. customcrystallized the product Boc-Cys(Trt)-NH2 from ethyl acetate and hexane (Yield: 100 g, HPLC Purity 98%, Chiral purity: 99.9% and D-Cys: 0.1%)

Sources & evidence

ORD record
ord-4ef677809d8445a3bdd50da0fecb7cde
Source dataset
uspto-grants-2015_10
Patent number
US09156885B2

Reaction notes

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