Ammonia → HCID 67091895, compound

HRID 1167276Notes

Reaction equation

HRID 1167276 reaction equation
[O:1]1[C@H:5]2[O:6][CH2:7][CH2:8][C@H:4]2[C@@H:3]([O:9][C:10](=[O:51])[NH:11][C@@H:12]([CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C@H:13]([OH:43])[CH2:14][N:15]([S:32]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)(=[O:34])=[O:33])CC(C)(C)CCNC(=O)NCC(OCC)=O)[CH2:2]1.O1[C@@H]2OCC[C@@H]2[C@H](OC(=O)N[C@@H](CC2C=CC=CC=2)[C@H](O)CN(S(C2C=CC(OC)=CC=2)(=O)=O)[CH2:67][C:68]([CH3:82])([CH3:81])[CH2:69][CH2:70][NH:71][C:72](=[O:80])[NH:73][CH2:74][C:75](OCC)=[O:76])C1.[NH3:103]>CO>[NH2:103][C:75](=[O:76])[CH2:74][NH:73][C:72]([NH:71][CH2:70][CH2:69][C:68]([CH3:82])([CH3:81])[CH2:67][CH:14]([NH:15][S:32]([C:35]1[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=1)(=[O:34])=[O:33])[C@H:13]([OH:43])[C@@H:12]([NH:11][C:10](=[O:51])[O:9][C@H:3]1[C@@H:4]2[C@@H:5]([O:6][CH2:7][CH2:8]2)[O:1][CH2:2]1)[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:80]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 67091709HCID 67091709, compoundHCID 67091776HCID 67091776, compound

Product 1

HCID 67091895HCID 67091895, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 22 mg (0.030 mmol) of a 1:1 mixture of ethyl (3S,4R)-1-[(3R,3aS,6aR)hexahydrofuro [2,3-b]furan-3-yloxy]-3-benzyl-4-hydroxy-6-[(4-methoxyphenyl)sulfonyl]-8,8-dimethyl-1,12-dioxo-2,6,11,13-tetraazapentadecan-15-oate and ethyl (3S,4R)-1-[(3S,3aR,6aS)hexahydrofuro[2,3-b]furan-3-yloxy]-3-benzyl-4-hydroxy-6-[(4-methoxyphenyl)sulfonyl]-8,8-dimethyl-1,12-dioxo-2,6,11,13-tetraazapentadecan-15-oate in 3 mL of 2M NH3 in MeOH in a sealed tube was stirred at RT. After 5 days the solution was concentrated in vacuo and the residue subjected to flash chromatography (SiO2, 93:7 CH2Cl2/2M NH3 in MeOH) to afford 11 mg (52%) of the desired product as a white foam.

Workup

  1. concentrationAfter 5 days the solution was concentrated in vacuo

Sources & evidence

ORD record
ord-821d0a482f1843108c0e934fabd9629e
Source dataset
uspto-grants-2003_09
Patent number
US06617350B2

Reaction notes

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