Sulfuryl chloride → 3-(1,5-Di(t-butoxycarbonyl)-3-(2-(t-butoxycarbonyl)ethyl)pentan-3-ylcarbamoyl)propanoyloxymethyl chloroformate

HRID 1397125Notes

Reaction equation

HRID 1397125 reaction equation
[C:1](=[O:43])(SCC)[O:2][CH2:3][O:4][C:5](=[O:39])[CH2:6][CH2:7][C:8](=[O:38])[NH:9][C:10]([CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].S(Cl)([Cl:47])(=O)=O>>[Cl:47][C:1]([O:2][CH2:3][O:4][C:5](=[O:39])[CH2:6][CH2:7][C:8](=[O:38])[NH:9][C:10]([CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:43]

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 86666537O-(3-(1,5-di(t-butoxycarbonyl)-3-(2-(t-butoxycarbonyl)ethyl)pentan-3-ylcarbamoyl)propanoyloxy)methyl S-ethyl carbonothioate

Product 1

HCID 866665383-(1,5-Di(t-butoxycarbonyl)-3-(2-(t-butoxycarbonyl)ethyl)pentan-3-ylcarbamoyl)propanoyloxymethyl chloroformate

Conditions

Temperature
0 °C

Procedure

To a solution of carbonothioate 74 (351 mg, 0.55 mmol) in ice-cold CH2Cl2 (3 mL) was added sulfuryl chloride (67 μL, 0.83 mmol) and the mixture was stirred at 0° C. for 3 h, after which the mixture was concentrated to dryness, providing chloroformate 75 as a colorless gum (334 mg, quant.) which was used directly in the next step: 1H NMR (400 MHz, CDCl3) δ 1.44 (s, 27H), 1.94-1.98 (m, 6H), 2.21-2.24 (m, 6H), 2.46 (t, J=6.6 Hz, 2H), 2.74 (t, J=6.6 Hz, 2H), 5.83 (s, 2H), 6.15 (s, 1H).

Workup

  1. concentrationafter which the mixture was concentrated to dryness

Sources & evidence

ORD record
ord-b40cf74172cd4d1c8b3a390910241334
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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