N-Cbz-N-methyl-2-aminoethanol → Benzyl 2-(di-tert-butoxyphosphoryloxy)ethyl(methyl)carbamate

HRID 1476290Notes

Reaction equation

HRID 1476290 reaction equation
[C:1]([O:5][P:6]([O:13][CH2:14][CH2:15][N:16]([CH2:27]C)[C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].OCCN(C)C(=O)OCC1C=CC=CC=1>>[C:1]([O:5][P:6]([O:13][CH2:14][CH2:15][N:16]([CH3:27])[C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 13279869N-Cbz-N-methyl-2-aminoethanol2×HCID 58080156Benzyl 2-(di-tert-butoxyphosphoryloxy)ethyl(ethyl)carbamate

Product 1

HCID 58080112Benzyl 2-(di-tert-butoxyphosphoryloxy)ethyl(methyl)carbamateYield 67%

Procedure

A similar procedure to that described for INTERMEDIATE 48 utilizing benzyl 2-hydroxyethyl(methyl)carbamate (INTERMEDIATE 51, 0.46 g, 2.20 mmol) as starting material was followed, with subsequent purification by column chromatography (ISCO, 12 g silica gel column, eluting with 0→100% EtOAc/hexanes) to give the title product (590 mg, yield: 67%).

Workup

  1. customwas followed, with subsequent purification by column chromatography (ISCO, 12 g silica gel column, eluting with 0→100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-190c2764b84844bcb48593e098d21e74
Source dataset
uspto-grants-2015_04
Patent number
US09018381B2

Reaction notes

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