Methyl chloroformate → HCID 59149868, compound

HRID 655588Notes

Reaction equation

HRID 655588 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]([NH:14][C:15]([N:17]2[CH2:22][CH2:21][N:20]([C@H:23]([CH2:35][OH:36])[CH2:24][CH2:25][N:26]3[CH2:33][CH2:32][C:29]4([CH2:31][CH2:30]4)[C@H:28]([OH:34])[CH2:27]3)[C:19](=[O:37])[C@@H:18]2[CH3:38])=[O:16])[CH:10]=[CH:11][C:12]=1[Cl:13].C(NCC)C>ClCCl>[CH3:5][O:4][C:2](=[O:3])[O:36][CH2:35][C@@H:23]([N:20]1[CH2:21][CH2:22][N:17]([C:15](=[O:16])[NH:14][C:9]2[CH:10]=[CH:11][C:12]([Cl:13])=[C:7]([Cl:6])[CH:8]=2)[C@@H:18]([CH3:38])[C:19]1=[O:37])[CH2:24][CH2:25][N:26]1[CH2:33][CH2:32][C:29]2([CH2:31][CH2:30]2)[C@H:28]([OH:34])[CH2:27]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8021DiethylamineHCID 44612251HCID 44612251, compound

Product 1

HCID 59149868HCID 59149868, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl chloroformate (9 mg, 0.1 mmol) was added at 0° C. to a solution of (S)-4-[(S)-3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-1-hydroxymethyl-propyl]-2-methyl-3-oxo-piperazine-1-carboxylic acid (3,4-dichloro-phenyl)-amide (example 106; 50 mg, 0.10 mmol) in dichloromethane (1 mL). The ice bath was removed, then after 30 min the reaction mixture was cooled to 0° C., treated with diethylamine (4 mg, 50 μmol), and evaporated. Chromatography (SiO2; dichloromethane to dichloromethane/methanol/25% aq. ammonia solution 90:10:0.25) provided the title compound (52 mg, 93%). White solid, MS (ISP)=557.1 (M+H)+.

Workup

  1. customThe ice bath was removed
  2. customevaporated

Sources & evidence

ORD record
ord-7e6114d33cae4bfe9e91fe46dfb9aa63
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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