Ethyl chloroformate → HCID 13079773, compound

HRID 2295329Notes

Reaction equation

HRID 2295329 reaction equation
Cl.NCC(N[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2C(O)C)C1)=O.[NH2:29][C@@H:30]1[CH2:49][CH2:48][C@@:47]2([CH3:50])[C@@H:32]([CH2:33][CH2:34][C@@H:35]3[C@@H:46]2[CH2:45][CH2:44][C@@:43]2([CH3:51])[C@H:36]3[CH2:37][CH2:38][C@@H:39]2[CH:40]([OH:42])[CH3:41])[CH2:31]1.Cl[C:53]([O:55][CH2:56][CH3:57])=[O:54].[OH-].[Na+]>C(Cl)Cl>[CH3:41][C@H:40]([OH:42])[C@@H:39]1[C@:43]2([CH3:51])[C@H:36]([C@H:35]3[C@H:46]([CH2:45][CH2:44]2)[C@:47]2([CH3:50])[C@H:32]([CH2:31][C@H:30]([NH:29][C:53](=[O:54])[O:55][CH2:56][CH3:57])[CH2:49][CH2:48]2)[CH2:33][CH2:34]3)[CH2:37][CH2:38]1

Participants

6

Reactant 4

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 22825173HCID 22825173, compoundHCID 70524041HCID 70524041, compound

Product 1

HCID 13079773HCID 13079773, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5 g of (20S) 3α-amino-5α-pregnane-20-ol in 500 ml of methylene chloride was added dropwise over 10 minutes under an inert atmosphere to a mixture of 15 ml of ethyl chloroformate and 45 ml of methylene chloride and the mixture was stirred for 30 minutes. 20 ml of N sodium hydroxide were added to the mixture which was stirred for 30 minutes. The mixture was decanted and extracted with methylene chloride. The organic phase was washed with water, dried, filtered and evaporated to dryness under reduced pressure. The residue was taken up in ether and the mixture was filtered to obtain 5.7 g of ethyl N-[(20S) 5α-pregnane-20-ol-3α-yl]-carbamate melting at ≃198° C. and having a specific rotation of [α]D20 =+25° ±1.5° (c=1% in methylene chloride).

Workup

  1. stirringwas stirred for 30 minutes
  2. customThe mixture was decanted
  3. extractionextracted with methylene chloride
  4. washThe organic phase was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure
  8. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-256cadef3d274c879fac191d220d8ae4
Source dataset
uspto-grants-1984_01
Patent number
US04424218

Reaction notes

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