4-Nitrophenyl 1,3-thiazol-5-ylmethyl carbonate → HCID 57037691, compound

HRID 433784Notes

Reaction equation

HRID 433784 reaction equation
[NH2:1][C@H:2]([C@@H:10]([OH:22])[C@@H:11]([OH:21])[C@@H:12]([NH2:20])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1C([N+]([O-])=O)=CC=C([O:32][C:33]([O:35][CH2:36][C:37]2[S:41][CH:40]=[N:39][CH:38]=2)=O)C=1>O1CCCC1.C(Cl)(Cl)Cl>[NH2:1][C@@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C@H:10]([OH:22])[C@H:11]([OH:21])[C@@H:12]([NH:20][C:33]([O:35][CH2:36][C:37]1[S:41][CH:40]=[N:39][CH:38]=1)=[O:32])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 98821474-Nitrophenyl 1,3-thiazol-5-ylmethyl carbonateHCID 15024277HCID 15024277, compound

Product 1

HCID 57037691HCID 57037691, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.133 mmol of (2S,3R,4S,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane and 0.147 mmol of ((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate in 10 ml of tetrahydrofuran was stirred at ambient temperature for 16 h. The resulting solution was diluted with 50 ml of chloroform, washed with several portions of 3N aqueous NaOH, dried over Na2SO4, and concentrated in vacuo. Silica gel chromatography of the residue provided the desired compound.

Workup

  1. washwashed with several portions of 3N aqueous NaOH
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b437bb1f5dae4ee195ff04b99ebec81d
Source dataset
uspto-grants-2003_12
Patent number
US06667404B2

Reaction notes

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