4-Nitrophenyl 1,3-thiazol-5-ylmethyl carbonate → (2S,3S,5S)-2-amino-5-(N-((5-thiazolyl)methoxycarbonyl) amino)-1,6-diphenyl-3-hydroxyhexane

HRID 1080520Notes

Reaction equation

HRID 1080520 reaction equation
[NH2:1][C@H:2]([C@H:10]1[O:15]B(C2C=CC=CC=2)[NH:13][C@@H:12]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:11]1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1C([N+]([O-])=O)=CC=C([O:38][C:39]([O:41][CH2:42][C:43]2[S:47][CH:46]=[N:45][CH:44]=2)=O)C=1>C1COCC1>[NH2:1][C@H:2]([C@@H:10]([OH:15])[CH2:11][C@@H:12]([NH:13][C:39]([O:41][CH2:42][C:43]1[S:47][CH:46]=[N:45][CH:44]=1)=[O:38])[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 98821474-Nitrophenyl 1,3-thiazol-5-ylmethyl carbonateHCID 15344175HCID 15344175, compound

Product 1

HCID 10812314(2S,3S,5S)-2-amino-5-(N-((5-thiazolyl)methoxycarbonyl) amino)-1,6-diphenyl-3-hydroxyhexane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 40 mmol of crude (4S,6S,1S)-6-(1-amino-2-phenylethyl)-4-benzyl-2-phenyl-3-aza-2-bora-1-oxacyclohexane in 700 ml of anhydrous THF was cooled to -40° C. and treated dropwise over a period of 1 h with a solution of 7.83 g (27.9 mmol) of ((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate in 300 ml of dry THF. The resulting solution was allowed to warm to 0° C. for 3 h, then to ambient temperature for 16 h. The solvent was removed in vacuo, and the residue was taken up in 700 ml of ethyl acetate, washed with three 150 ml portions of 1N aqueous NaOH and one 150 ml portion of brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. Purification of the residue by silica gel chromatography using methanol/chloroform mixtures provided the desired compound mixed with its regioisomer. A second chromatography using 1-3% isopropylamine in chloroform provided 5.21 g of the desired compound which solidified upon standing.

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with three 150 ml portions of 1N aqueous NaOH and one 150 ml portion of brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-f18885580f074a6cb32c6d2fa2e7c02c
Source dataset
uspto-grants-1996_12
Patent number
US05580984

Reaction notes

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