HCID 11269582, compound → HCID 69431427, compound

HRID 458322Notes

Reaction equation

HRID 458322 reaction equation
[N:1]([CH2:4][C@@H:5]1[CH2:9][C@@H:8]([S:10][C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][NH:6]1)=[N+]=[N-].Cl[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH2:34]([O:33][C:31]([N:6]1[CH2:7][C@H:8]([S:10][C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][C@H:5]1[CH2:4][NH2:1])=[O:32])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 11269582HCID 11269582, compoundHCID 86584840HCID 86584840, compound

Product 1

HCID 69431427HCID 69431427, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S,4R)-2-azidomethyl-4-tritylsulfanyl-pyrrolidine and benzyl chloroformate/N-ethyldiisopropylamine in CH2Cl2 (see cabamate synthesis, Method A)—followed by Staudinger reduction gave (2S,4R)-2-aminomethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid benzyl ester as white foam, MS: 509 (MH+).

Workup

  1. customcabamate synthesis, Method A)—followed by Staudinger reduction

Sources & evidence

ORD record
ord-426f4d72a10d4daf90b0ccdff631b609
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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